Sales Tech Thought Map Series

Sales Technology Thought Map

~ Sales Technology Thought Map ~ Categories and market dynamics in the world of software are always developing and evolving with continuous fluidity. As an investor in the space, adhering to Warren Buffet’s famous adage of “investing in what you know” definitionally requires keeping a real-time pulse on the ebbs and flows of the space. This is hard to do in software land. The space is massive (hundreds of billions in annual spend). It’s incredibly dynamic, transforming at the speed of innovation. Its reach is pervasive, influencing almost every element of how businesses and consumers operate today. At PeakSpan, we firmly believe in Buffet’s ethos, and believe that “knowing” a category means cultivating an understanding that extends far below the surface level. Asserting expertise in our view requires intense focus and experience-informed specialization, built up over a long period of time. Because the software universe is so massive, and change happens perpetually, knowing the entire universe at a level of depth required to claim expertise is simply not credible. We embrace this axiom, which underpins a central pillar of our philosophy as investors. Narrowing the aperture enables every element of a more confined picture to be understood and appreciated with significantly more clarity. We deliberately limit the number of sub-segments or themes that Partners at our firm can focus on to three or less. I’m humbled to lead PeakSpan’s Sales Tech practice and have had the privilege of living in, investing behind and working shoulder to shoulder as a thought partner to some truly exceptional entrepreneurs and monster businesses over the last decade. My mission is to become as steeped as humanly possible in the happenings of the space to garner a sense for the current zeitgeist in market and drive experience-informed impact as an investment partner. I spend a massive amount of time synthesizing a perspective on what is happening, which influences are most impactful and how it all might come together to shape the landscape. The output of those discussions directs our focus as investors towards the things we believe are or will become strategic over the coming quarters and years. These can be specific sub-segments, business models or even changes in behavior or workflow that effect how selling or buying is approached. Compartmentalizing these views is challenging, but we’ve pushed ourselves to do just that in order to share our thoughts and views on the space. We’ve abstracted our perspectives up into a handful of overarching areas of focus which we will share with you all over the coming weeks in a five-part series, with each installment exploring one of these overarching themes– and the sub-themes comprising it – in a summary dissertation-like format, with indicative vendors mapped under each. To be clear, the resulting “thought map” is not a comprehensive nor exhaustive map of the category but is rather meant to provide insight into some of the exciting trends we are seeing in the space. The vendors mapped herein represent emerging innovative businesses we think are driving change in the space, and we have excluded incumbent providers despite some of them having functionality that might play into a given theme. The first part of our thought map examines a foundational competency in the world of sales – value proposition articulation. “Okay, we’ve got this amazing solution to share with the world… now, how do we convey its amazingness?”

Part One: Value Proposition Articulation “If the message is relevant, then it concerns them. If the message is important, then it concerns them deeply. If the message is urgent, then it concerns them deeply, now.” ~ Flint McGlaughlin The concept of value is foundational to any transaction; and always has been. Be it the barter economy hundreds of years ago or grabbing a pack of gum at the bodega, any exchange is fundamentally based on an understanding – potentially perceived wildly differently by the parties on either side of the trade – of the underlying worth of whatever is being dealt. The ways in which value is communicated today is of course very different from years prior; advancements in technology and shifts in communication preferences over the last few years have been so dramatic that the way in which things were done even a decade ago now seem anachronistic as compared to current status quo. The ways in which we educate ourselves, the media by which we engage and the products and services we use today have experienced notable change, driven by innovation, and enabled by software. Information is now everywhere and free to consume. Digital channels and virtual interactions have usurped a handshake and a coffee as the dominant modalities for business communication. Products are available online; discoverable, searchable, learnable, and often testable prior to any human interaction taking place or purchase decision being made. Human beings have never liked being “sold to”, and the caricature of the sleezy used car salesmen barking “WHAT DO I HAVE TO DO TO GET YOU IN THIS CAR TODAY!?!?” has never been appealing. The buying process today is significantly more self-guided and laden with primary research and independent ingestion of user-generated feedback than it has ever been. Buying experiences have become increasingly self-service in nature, especially for technology-focused offerings, enabling a buyer to navigate the entire evaluation journey and ultimate purchase experience on their own. The phrase “Product-Led Growth” was first coined in 2016 but has quickly risen to prominence in technology circles in less than a decade to define and describe a new way of buying. Which definitionally requires a new manner of selling. The theme of interest in the first part of our Sales Tech Thought Map series we describe as Value Proposition Articulation. It encompasses three sub-themes, all of which touch on an element of enabling the aforementioned new paradigm shift in the world of selling. We’ve observed a number of exciting vendors and new categories emerging over the last few years, but will touch on a few discrete competencies we believe are strategic and sustainably valuable in this editorial – namely startups attacking the challenges and opportunities associated with i) Supporting efficient, effective and personalized engagement at scale; ii) Enabling and driving the new “product- - 2 -

led” sales motion with a focus on the solutions/sales engineering teams and the buyer; and iii) Enhancing the buyer experience by serving up relevant collateral and content, at the right time in the sales process, focused uniquely on the buyer’s needs. Engagement Efficiency / Sales Process Automation Engagement today is defined by email as a central pillar of business communication, flanked by social channel, on-site communication, and mobile-first conversations. Inherently asynchronous in nature the majority of the time, this new dialogue standard supports the ability to leverage tools, methods and workflows that hyper-charge efforts and provide “sellers” with the ability to cast a much wider net and touch a far broader potential audience. By virtue of all of these things, however, many channels and approaches to outreach (initial outreach in particular) have become saturated with “spray and pray” attempts at feigning personalization and failing miserably as manifested by [INSERT NAME HERE] and blasted to the billions. To stand out and garner audience in this new normal, businesses need to find ways to i) be efficient in their approach to contacting high volumes of potential prospects, ii) meet said prospects in the places they live and spend their day, iii) deliver a perception of a one-to- one, individualized conversation, iv) surface and address an acute pain point or need to garner attention, v) address said need or want with relevant a piece data, information, promotion or offer to help reduce friction in the buying process, and vi) drive urgency as to why now is the time to cross the finish line on the marathon that is the path to purchase. - 3 -

Engaging with prospective buyers on the channels they live in, efficiently, effectively and at scale with the perception of a one-to-one front end dialogue, while actually being a one-to-many software- enabled back-end process is the core focus of solutions in this theme. We’ve seen a number of vendors addressing different parts of this conundrum with intelligent solutions that tech-enable the workflow of a seller to compete and standout in today’s market environment. Platforms supporting outreach efficiency – automating tedious or repetitive tasks across email and other outreach modalities to free up rep time to focus on higher level undertakings – are quickly establishing a new status quo for how to approach a discussion with a prospective buyer in today’s market with great resonance, improved efficiency and increased efficacy. We believe some of these tools are prime candidates for acquisition by broader incumbent vendors with comprehensive platforms, however, the outcomes-based positioning of the category and clear ROI the solutions are delivering justifies the standalone persistence of several sub-competencies within this theme in our view. Product-Led Enablement As sales processes have shifted from primarily encompassing physical meetings and largely siloed conversations to examination of technical platform merits and digital-first solution collaboration, the constituents involved in the process, as well as the primary focus of the process itself have evolved. Whether selling a high-velocity, inexpensive self-service platform in a wholly PLG motion or a more complex, expensive solution sell, buyers now expect to be able to evaluate products in a much more granular, hands-on way. They expect information transparency and having the opportunity to see, feel and understand the platform they are considering. Effective sales motions today are cohesive, cross-functional and product-centric, and as the platform being evaluated has continued to rise in prominence (versus the seller trying to sell it), the role of the pre-sales function has become more and more strategic. The sales engineering, solutions consulting, pre-sales orchestration function – whatever nomenclature your organization uses to describe the part technical, part sales-oriented team involved in configuring and delivering a demo experience, answering - 4 -

technical inquiries, devising implementation strategy, etc. – has become a more integral part of the GTM motion for many companies in this PLG-oriented era we find ourselves in. Whether an organization offers the ability to trial a product directly or simply wants to show the solution via a demo that will hold water in today’s environment, delivering an experience that is seemingly individualized and configured to the needs and pain points of the prospect, addressing their specific use case while articulating value in accordance with the jargon in their vertical has become a strategic arrow in the selling organization’s quiver. We’ve observed a new cadre of vendors emerge recently which seek to reduce friction and streamline the evaluation process in a product-centric way. Everything from development of interactive demos and personally configured trial environments through digital collaboration portals housing pertinent information related to the use case in question – in our view, leveraging software to provide insight into what prospects can expect post-sale from a solution value perspective will become a ubiquitous competency for organizations of all shapes and sizes over the coming years. Delivering insight into seemingly white-glove, bespoke product experiences prior to transacting has become a strategic differentiator and should emerge as a core competency going forward. Buyer-Centric Content The Sales Tech team at PeakSpan has a great relationship with – and immense amount of respect for – Andy Paul, a seasoned and decorated operator in the sales arena who has played the role of everything from individual contributor to team leader to founder/CEO to podcast host, all with insane efficacy. Andy has authored multiple books about various dynamics in sales and his newest missive talks about the concept of “selling in”, which in essence details the process of understanding the buyer’s needs, playing the role of enabler to support the buyer’s decision process, and not succumbing to the cold and calculated lemming-inducing tactics preached as gospel in the sales arena at the expense of losing your individual uniqueness as a person and salesperson. People buy from folks they trust, that are helpful, authentically striving to provide insight and information to let the buyer make an informed decision based on his or her needs. An innovative category of vendors has emerged which are seeking to enable this ethos with software, developing buyer-centric content focused on providing more clarity to help answer the fundamental questions the buyer has and serving it up on the channels and in the workflows where the prospective buyer spends their time. Content has always been queen, and this group of innovative startups are taking a content- centric approach to buyer enablement, delivering a very valuable service from our perspective. And one that has the potential to persist for years to come. - 5 -

Closing Thoughts The “thought map” is not meant to provide a comprehensive view of the ecosystem nor these sub- segments in question, but we believe elucidates some exciting businesses driving a new wave of buying and selling motions in market today. We have tremendous respect and admiration for the incumbent providers who have paved the way in sales tech land and continue to drive innovation broadly in the space, but have focused our views here on the vendors and themes we view as having the potential to be the next cadre of category influencers and market-moving dynamics that will define the next decade of growth and maturation. - 6 -

Part Two: Data-Informed Decision Making “I keep saying that the sexy job in the next 10 years will be statisticians, and I’m not kidding.” – Hal Varian, Chief Economist, Google We live in the Information Age, defined by Merriam-Webster as “a time in which information has become a commodity that is quickly and widely disseminated and easily available especially through the use of computer technology.” Knowledge previously recorded on paper and living in libraries is now digitally domiciled and hovering in the cloud. Information is accessible from anywhere, at any time – and the sheer volume of it being captured has exploded. We’ve produced more data in the last two years than we did throughout the entirety of human history before that. The only thing growing as rapidly as data itself, fortunately, is our ability to process it. Computing power is increasing at an exponential rate (literally) – for context, the latest iPhone has over 1.5 billion times more processing power than the NASA supercomputer that landed man on the moon. Data itself is a commodity – like a bag of grapes anyone can grab from their local grocer for a few bucks. But winemakers have shown that those same grapes, when harvested in a specific way, blended precisely with other ingredients, and fermented for a particular amount of time, can be transformed into a highly valued fine wine. But renowned vino producers didn’t just get lucky the first time they made a batch. The masters will tell you their best product is the result of years of iteratively fine tuning their process, maniacally focusing on understanding the variables at play and analyzing how they interact with each other to optimize the blend with each successive vintage. Analogizing grapes to data might be a bit of a stretch, but hopefully the premise is clear. Leveraging data to make strategic decisions is important… no shit, Sherlock! But the reality is we are still in the early innings of the information revolution, and while more organizations are beginning to weave data-informed decisioning into the fabric of company culture, transforming behavior and ushering - 7 -

in a shift in mindset takes time. Regardless of how powerful or impactful a solution claims to be, buyer readiness to adopt requires trust. And the most effective way to garner trust is to deliver clear, tangible value. The world isn’t suffering from a lack of insanely smart, overly educated individuals trying to change the world with big data analysis and machine learning. Countless new startups equipped with billions of dollars of investment are focused on the opportunity. But who cares how algorithmically amazing a software solution is or how much analytical horsepower a platform has if the value it provides to customers is nebulous? Innovation without impact is nothing more than the next bright shiny penny. The platforms we believe are best positioned to gain traction over the next few years are those focused on harnessing the power of data and applying it pragmatically to influence specific, well- defined business outcomes. Part two of our thought map series examines three sub-segments comprising vendors leveraging data-centric approaches to help go-to-market teams answer some of the most fundamental and impactful questions they face today. How can we sell more effectively in an increasingly product-led era as the buying process is evolving? How can we arm our sellers with context about this prospect to increase their chances of conversion? How likely are we to close this account and where do we think we’ll finish for the quarter and year? High Velocity Sales Assist The rise and proliferation of product-led growth – and more broadly the increasing pervasiveness of self-serve models – has enabled individual business users across functional groups to get up and running with productivity applications, workflow optimization solutions and broader enterprise platforms with the swipe of a credit card. Classic top-down enterprise software buying and selling is not going anywhere for a while, but we’ve clearly entered an era where almost every category of software has one (or many) vendors attempting to disrupt the landscape with a bottoms-up, friction-light GTM approach supporting the ability to purchase and deploy a solution with little or no direct human involvement. Nobody enjoys the feeling of “being sold to, especially in an in-your-face, pop-up-ad kind of manner, but this has evolved in a much more nuanced way over the last few years. Now that prospective buyers can – and very often do – ingest massive amounts of information comparing product capabilities, pricing and value proposition before ever engaging with a given business directly, the role of the seller in the buying process needs to change. - 8 -

Automation and seamless deployment models have enabled this new wave of procurement, and effective sales motions must embrace this dynamic and evolve to provide value to buyers across the modern path to purchase. The roles of the seller in this inherently more buyer-led journey needs to shift from proactive engagement and explicit orator of value proposition to responsive enabler and implicit buyer-assist. When a prospect (or current customer) interfaces with the platform itself far more frequently than with a human being, understanding the needs of the buyer necessitates “listening” to the data produced as the user engages with the solution. A new and burgeoning category has emerged comprising businesses focused on not fighting, but supporting this shift, and strategically software-enabling these modern sellers to be better listeners. We believe this is one of the more pronounced changes in the buying motion over the last decade, and platforms that empower sellers to adapt and transition with the times in an elegant way will garner widespread adoption over the coming years. Contextual Insights Every company leverages some tool or vendor for sales data. Most use ZoomInfo – often in combination with other data providers – to supplement an email address with a variety of salient and not-so-salient data points that help piece together the puzzle of who the person on the other end of the email/phone call is. Data in a silo can be tactically helpful, but arming reps with the most pertinent context to ensure every interaction with a prospect is engaging and productive is highly strategic. Delivering these insights in the most digestible way, to the right individual, at the right time, without disrupting their existing workflow is as important as the information itself. Any tool that introduces friction or creates overhead for end users will struggle to garner adoption. As the amount of data available continues to explode, being able to sift through the noise and surface the right piece of information in the context of the situation is tremendously impactful. The vendors in this segment that we believe are paving the way for a new type of truly engaging experience are positioned as much more than data providers, but rather thought partners to your GTM team. One of only two shameless portfolio company plugs in this series goes here to Cognism, a global leader in sales intelligence, providing businesses with data, tools to action the data and the contextual insights required to provide sellers with the best chance at having a great conversation. This focused, outcomes-based approach has catalyzed the business to grow over 10x in less than three years and will push them past $100M ARR in the near future. Context is queen, and the queen is valuable. - 9 -

Revenue Predictability The finger in the air guessing game to answer the age-old question of “Where will we end up this quarter?” no longer plays. Given the massive amount of data we now capture across the sales cycle, doesn’t it seem a bit archaic that most companies still track pipeline opportunities using just a handful (typically seven) of high level, round number percentage stages? “25% for qualified”… yeah, that seems fair. Every opportunity has specific nuances, and I guarantee some of those prospects in that 25% bucket are more qualified than others. Now that we are able to track more and more data related to rep activity and capture information from every interaction/touchpoint with a prospect – in an automated way – opportunities can be analyzed with much more than seven stages of granularity. There is a new crop of vendors leveraging innovative analytical approaches to surface signals gleaned from the breadcrumbs of data produced across the buyer journey to form a much more detailed view of pipeline health. Like grading a test on scale from 1-100 versus using the five-tier “A” through “F” letter grade range, these approaches seek to incorporate a multitude of variables to provide a highly refined view of where each engagement stands. Organizations adopting these solutions are also better positioned to become increasingly agile with budgeting and real-time with forecasting as they scale. The local weather woman doesn’t just guess what tomorrow will bring based on gut feel, she listens to the data to make an informed prediction. Sales should be no different. - 10 -

Part Three: Strategic Knowledge Flow “Tell me and I forget, teach me and I may remember, involve me and I learn.” - Benjamin Franklin Launching a business is as trying as it gets, and every step of the journey brings a distinct set of challenges and opportunities. The startup phase is characterized by firsts – the first version of the product, the first outside hire, the first closed deal. Progress in the early days is almost always a byproduct of grit and creativity, finding scrappy ways to make things happen. Crossing the chasm from startup to scaleup requires process, structure, and standardization to ensure the business matures with predictability and consistency. Software companies don’t produce physical goods. They don’t have inventory. They don’t manage manufacturing dependencies. There is no assembly line to optimize. The business value is instead the amalgamation of the thoughts and ideas of the brilliant minds on the team, which is most valuable when synthesized cohesively and applied uniformly to achieve a common goal. Supporting and enabling the growth of the organizational knowledge asset will ultimately play a pivotal role in catalyzing the growth of the business. Knowledge – related to the company’s value proposition, market positioning, competitive landscape, go-to-market strategy, and a laundry list of other meaty topics – becomes the fuel required to power the organizational engine in the scaleup phase. That precious resource resides only in the minds of the founders/early team initially but must be extracted from the heads of a few and disseminated methodically across the entire organization as it expands. - 11 -

Employees get exposure to the amorphous knowledge blob in the early days by sitting beside the founder(s) and naturally absorbing valuable information via observation and osmosis. Employee number 100 won’t have that same luxury, as information flow becomes inherently diluted as the team grows. Know this. Plan for it. Focus on it. Establish a system to capture institutional know-how programmatically and deliver it in a structured manner to provide every new hire with the best chance of being successful. This is easy to say, but very hard to do. The good news is that software can help! The third installment of our thought map series examines this overarching theme that we’re calling strategic knowledge flow. This is certainly a large, amorphous, multi-faceted area of the software universe that extends into and overlaps with many other categories, but we’ve identified and examined three sub-segments for the purposes of this missive. At the highest level, the vendors playing in these spaces are aimed at supporting the flow of valuable information across an organization as it scales, as effectively and seamlessly as possible. Each sub-segment discussed herein is attacking this dynamic challenge from a different vantage point, respectively focused on a distinct and well- defined use case. Video-Centric Productivity COVID-19 catapulted video-based interactions into the foreground as the new de facto standard in business communications. Remember when scheduling a phone call was typical?!?! I certainly do! Whether you prefer hopping on a Zoom “call” or chatting on your cell, video is here to stay. We’re still in the early days of this new video-centric era, but the tectonic shift it has influenced already is pervasive. For starters, these new channels kick off new forms of data – both structured and unstructured – all of which can be valuable for different reasons. This requires new methods to capture it all and new strategies to make sense of it in a cogent way. Software continues to eat more and more of the world. But it does so over time and in waves, not immediately and comprehensively on day one. We’ve seen a recurring dynamic - 12 -

whereby the first things to change tend to be driven by automation of tactical but impactful tasks that were previously largely manual. Driving workflow efficiency or increasing speed of execution provides a benefit that is clear and tangible, easy to define and hard to deny. This is essential for new approaches and technology platforms to gain traction initially and experience widespread adoption thereafter. Technology that frees up employees’ time to focus on more strategic higher- level activities was attractive ten years ago, still is today, and will be ten years from now. Inputting data into a CRM, for example, has always sucked and never been fun. But it has always been essential and needs to be done with high fidelity. This monotonous process has evolved dramatically in the last five years, as automation has engulfed and augmented more and more of the process. We believe technologies similarly focused on the “low hanging fruit” opportunities to make organizations operate more efficiently in the current video-centric age of business communications will be those that garner early traction and momentum. Being able to eliminate the need to ever take notes during a meeting again – I think all would agree… is valuable. Pen and paper have given way to laptops and tablets for faster scribing, but the fastest typist in the world has no way of capturing the entire nuance of a virtual meeting happening on video. But software can, and a cadre of ambitious entrepreneurs identified this logical and strategic opportunity early on. Solutions in this bucket have quickly gained traction and experienced viral adoption in market, led by a few vendors that are out to an early lead. This will become a must-have tool in the sales tech toolkit in short order for any company conducting business in a distributed/virtual or hybrid environment. The next phase of innovation in this category in our view will revolve around moving beyond simple data capture and process automation toward robust analysis of the data to glean insights and surface calls to action as the ultimate output. Partner Enablement Selling through partners is always elegant in theory. Feathering in a new high margin revenue stream without the additional overhead and new hires a typical direct sales motion requires? Yes please – sign me up! Unfortunately, the promise of partner-led strategies often sits in stark contrast to the reality. There are myriad reasons partner motions can and do fall short, but two of the most pernicious issues we see crop up time and again, regardless of the end market being targeted, solution being sold, or buyer persona being courted, are: 1. Insufficient Information: The partner’s sellers don’t have the information needed to effectively articulate the value proposition in a powerful way. 2. Insufficient Incentive: The partner’s sellers aren’t properly incentivized to change their behavior and sell the new solution instead of (or in conjunction with) their own. You can’t expect someone to do something if you don’t tell them how to do it and give them the tools they need to do it successfully. Asking your kid to cut the lawn but not giving them a mower and a crash course on how to use it wouldn’t make sense. And while there may be some kids out there who are psyched to get out there and cut the grass purely for the love of the game… I’ll - 13 -

admit that I wasn’t champing at the bit to mow our lawn, unless there was a shiny $10 bill with my name on it for doing so! Whether the goal is a well-kempt front lawn or a productive partner channel, it doesn’t matter; supplying the information and the motivation to make it happen is the name of the game. A new cadre of thriving businesses has emerged focused on leveraging software to align knowledge and incentives with organizational objectives to optimize the partner channel. We believe several companies are well-positioned to transform the status quo and redefine what best- in-class partner enablement looks like over the coming years. Outcomes-Based Learning Building a productive, efficient, consistent go-to-market engine at scale requires a dedication to process-centricity and a commitment to making learning a continuous prerogative, not a once a year/quarter initiative. Whether it be architecting an effective onboarding program or establishing the infrastructure to support ongoing training and real-time enablement, the most effective programs we’ve seen are underpinned by continuous learning. The most successful approaches we have seen are straightforward, learnable, and repeatable, aimed at arming both new joiners and fully ramped reps with the tools and knowledge they need to immerse themselves in the sales motion and constantly refine and optimize their craft to sustain productivity. The best way to do this is to develop programs that are focused on specific outcomes. Things that are definable and have proven to be influential in the sales process. Software has enabled businesses to capture and analyze every element of the modern sales cycle, surfacing specific things that top performers do that are correlated with success. Activities and methods that can be clearly tied to productivity and closed business – things like mastering the company pitch deck or - 14 -

demonstrating command of objection handling with battlecards – should be built into the program to ensure reps learn impactful skills as they ramp and hone those skills over time as new strategies are proven more effective. This structure also ensures that the leaders of the GTM organization are focusing their one-on-one coaching time on further developing higher level skills versus micromanaging tactical task execution. For software companies, the most important thing to equip your sellers with is strategic knowledge – about the product, the most effective way to execute the motion, the most impactful way to articulate differentiation. Importantly, this detail must be delivered in a manner that is digestible, and integrated into the existing workflow of the seller to ensure it can be digested without introducing friction as much as possible. Lastly, aligning incentives and providing a clear, attractive reward for performance is essential to operationalize that elegant theory into practice. The second and final portfolio company plug in this series goes here to Rallyware, a business that has rapidly established an early leadership position in the next-gen partner enablement arena. Rallyware provides the right information, to the right individual, at the right time, in the right format to give them what they need to get the job done. Delivered seamlessly into the existing workflow of the seller – often beamed directly onto their mobile phone – and stapled with a Godfather-esque “offer they can’t refuse” to make sure the seller truly cares. Equip your partners with top-of-the-line mowers, delivered with an intuitive user manual and comprehensive guidance on the unique ins and outs of your plot of grass – and you’ll have the most pristinely manicured lawn in the neighborhood. - 15 -

Part Four: Optimized Execution “Having a vision for what you want is not enough. Vision without execution is hallucination.” - Thomas Edison Working uniquely with businesses at what we define as the emerging growth phase of company development at PeakSpan means that every company we partner with has answered a lot of the existential questions startups are faced with: Can we build it? Will they buy it? Can we sell it on terms that make sense for us as a business? These fundamental issues – related to core technology/product, market opportunity/adoption, business model viability – represent binary risk levers. They simply must be satisfied, or they will kill the company. Navigating the whitewater rapids of the startup phase successfully means you’ve worked hard to mitigate and strip away those binary risk vectors. That’s the point in the company journey arc where we come in. While the next leg of the voyage is certainly no easier, less grueling, nor without risk, the type of risk encountered is very different. The scaleup phase is all about moving from ad hoc to repeatability, from volatility to consistency, and from creative and scrappy to systematized and process centric. Success involves intentionally placing bets in the right places, doubling down at the right times, and understanding the natural limitations of what the business can palpably digest without self-inflecting debilitating levels of indigestion. At the end of the day, making the right decisions related to where to add resources, ramp up investment and expand the team is only half the battle. No matter how attractive a market opportunity may be, how differentiated a platform appears, and how much capital a company has access to, if your team can’t execute, nothing else matters. Sustained execution is as critical as anything else in growth company development. It’s an essential ingredient in the recipe for resilient value creation. And sales execution in particular will end up either inhibiting or driving the ultimate value any business will achieve. - 16 -

Strong sales execution is the result of so many nuanced variables which can vary dramatically based on value proposition, price point, industry vertical, etc., making it impossible to develop a playbook and prescribe an approach that will work for every company. Different GTM organizations – and the individual sellers comprising them – operate in different ways, using different tools, employing different strategies. However, there are a few things that almost all GTM teams need to do to sustain productivity and execute at a high level in the modern era. First, you need to align on your ideal customer profile, find them, engage with them, and track progress of those engagements. Next, you need to learn how to engage most effectively, and continuously refine and optimize your approach. Finally, if all else goes well, you need to get prospects to sign on the dotted line, and hopefully do so again and again in the future to maintain and expand the relationship. There is a lot more to it than that of course, but each of these things are unequivocally critical ingredients to achieving success and sustaining execution as a GTM organization. The next installment of our thought map series explores three sub-segments of the sales tech universe which are aimed at software enabling these essential drivers of best-in-class sales execution. Generative CRM Salesforce turns 25 in February of next year and is arguably the most influential B2B software business that has come onto the scene over that time. They created the modern CRM market as we know it today, have dominated it for nearly two decades, and have played an instrumental role in establishing SaaS as a household acronym understood well beyond the tech community. Salesforce is synonymous with CRM, and deservedly so – the company has more market share than the next four vendors in the space combined. The ways by which organizations record, track and manage their customer relationships has transformed as dramatically as any other component of sales over the last five decades. The note card laden rolodex of the 1950s gave way to the introduction of mainframes in the 1970s and databases in the 1980s, all of which were precursors to the first “contact management software” platform launched by Conductor Software in 1987 and subsequently the first “sales force automation” platform, pioneered by Siebel in 1995. Marc Benioff founded Salesforce in 1999 and 20 years later it became the first cloud computing company to breach $1 billion in revenue. After 73 straight quarters of revenue growth – yes, that is over 18 years, and yes, that’s a mind-blowing statistic – Salesforce surpassed SAP in Q2 2022 to become the largest enterprise software company in the world. Salesforce’s revenue today is north of $30 billion. To say the 2023 version of Salesforce’s CRM platform barely resembles the solutions brought to market by the early entrants not too long ago is a laughable understatement. Both the company’s financial performance and platform breadth/depth have been expanding at near exponential rates. As one might expect from a company that has increased revenue by a factor of more than 600x in the last two decades, Salesforce has driven immense transformation in the space along the way. Love them, hate them, love to hate them… it doesn’t matter; the impact SFDC has influenced is undeniable. - 17 -

And yet, despite the magnitude of change the category has undergone since the company stepped onto the field, the pace of innovation we are witnessing now is so significant that we believe it has the potential to nurture category evolution in the next 20 years that is even more dramatic. Over the last 10 years, AI has outperformed Moore’s Law – the longest standing assertion related to pace of technology innovation which suggests that computer performance (speed, processing power) will double every two years. While this was largely on point for the last 50 years, performance of AI systems has been doubling every six months for the last decade. We’re calling this disruptive next-generation segment Generative CRM, which we believe is apropos and descriptive of the value proposition these avant-garde platforms seek to deliver. Generative AI has rapidly become the most pervasive buzz word in Silicon Valley, and for good reason, as it pushes technology beyond observation, analysis, and insight, to creation for the first time. Early applications of Generative AI are primarily focused primarily on creating data and content in the form of bespoke text, vibrant imagery, dynamic audio/video, and even software code itself. Generative CRM vendors are similarly focused on creation, but instead of data, these businesses are creating revenue opportunities. - 18 -

Generative CRM platforms work by ingesting all available structured and unstructured data points, contextual cues and interaction details related to customers and prospects, and then analyzing that information to glean valuable signals from the vast array of noise. These signals independently can be valuable and predictive of a prospect’s propensity to engage or an ICP’s intent to buy. But Generative CRM platforms take it a step further and examine not just what these signals independently imply, but what the interactions of those various signals together suggest on a multi-variate basis. Similar to the movie Inception, in which the main characters leverage a futuristic technology solution to extract valuable pieces of information from “a dream within a dream”, these platforms seek to reveal valuable revenue opportunities by examining the “signal within the signals”. This is incredibly powerful, as it enables GTM teams to attack opportunities based on things that were previously unknowable. Conversational Intelligence The most consistent, predictable, productive sales organizations – and the best performing sellers – commit to an ethos of continuous improvement, constantly seeking to enhance tactics and employ new strategies to optimize execution. Operationalizing this mindset requires adopting - 19 -

training and coaching as ongoing priorities and always-on initiatives, learning in real-time what is working and how to tweak/enhance approach accordingly. Even the best sales leaders only have so many hours in the day to shadow the sellers on their teams and listen in on calls/meetings to provide feedback to help them improve their skills. Software has enabled GTM organizations to complement human effort with machine learning to analyze not just a handful of interactions, but every single word spoken across every touchpoint with a prospect. Gong has quickly become one of the leading “new incumbents” in this area, as conversational intelligence has ascended to become a table stakes competency for organizations of all shapes and sizes today. This category is still nascent and burgeoning, and the ability to seamlessly integrate systems of record being used across the enterprise now enables businesses to “listen” to data being produced across all functional groups and incorporate key learnings, effective positioning, and current messaging into their GTM strategies. Technology should always be an enabler of success, not the primary driver of that success. Leveraging software to complement the efforts of the team – not replace them – has proven to yield some of the most strategic applications of innovation that we’ve seen. Freeing up time so team members can spend every waking minute on the highest value activities – things the robots can’t do (yet) – delivers clear, tangible value, and this segment is a great example of that. Enabling a VP of Sales to spend as much time as possible engaging with their team and coaching their reps - 20 -

to develop their higher-level skills versus wading through hours and hours of conversational data in the hopes of extracting pertinent actionable insights is incredibly strategic and will be for years to come. Adaptive CPQ & Renewals Automation Friction is the enemy of execution in any sales process, regardless of sales cycle length, price point or industry vertical. The last step in the process of any sale is the proposal stage, and when a prospect raises their hand to say they’re ready to buy, you need to be ready to present a framework that makes sense, share it with them in a digestible format, and maintain agility by being able react/respond to make changes quickly and efficiently as you drive to closing. While the longstanding configure, price, quote (“CPQ”) arena rarely graces the cover of TechCrunch, we believe the innovation happening in this segment is notable. Several vendors in the space are catalyzing a transformation of the status quo, evolving from PDFs being the predominant medium for contracting to a modern, dynamic format that is integrated into all relevant systems of record (CRM, accounting/finance, ERP) to ensure changes made to a given proposal ate automatically tracked across the business. Inking the initial deal, however, is only half the battle. Software-as-a-Service is aptly named… SaaS vendors are not selling hard iron on premise in a one-time fashion then collecting 20% maintenance thereafter. SaaS is definitionally software sold as a service, priced as a recurring subscription. By virtue of that, maintaining, renewing, and potentially expanding a customer’s business is something that needs to be earned continuously. - 21 -

Providing ongoing value and securing the renewal of course involves engagement from numerous functional groups (Customer Success, Account Management, Product, Finance), but the same notion noted above to begin the section remains true in the land of renewals/upswells – friction is the enemy of execution. Modern enterprises now leverage dozens and dozens, sometimes hundreds, of software products to supercharge their efforts. As a result, simply getting ahead of what subscriptions need to be renewed, when, and for what amount, can be a daunting task to manage. Fortunately… there’s now software for that! A new crop of vendors has emerged in recent years focused on automating the renewal/upsell process, improving the experience for both customer and provider by removing friction wherever possible. Today, this primarily involves providing the buyer with all relevant information required to make the keep, cut, or buy more decision, and ultimately making the (re)purchase process itself as seamless as possible. Human beings increasingly prefer to self-educate and self-serve, more frequently demonstrating a propensity to avoid human interaction and drive decisioning in a self-guided manner wherever possible. The vendors in the burgeoning renewals automation segment that we have been impressed with cater to that propensity and deliver mind-boggling ROI to their customers in the process. While at first blush the value proposition espoused by these platforms may seem tactical, make no mistake about it – reducing friction across the buying/renewing/upselling journey is highly strategic, and the momentum the early leaders in the space are experiencing is the pudding that bears the proof. Similar to the Revenue Predictability segment discussed in part two of the thought map series, a tangential but very important benefit these solutions deliver is their ability to support customers in becoming more dynamic, real-time, and data-informed in their forecasting and budgeting approach. Moving towards an agile forecasting methodology enables organizations to be more deliberate and intelligent in their resource allocation decisioning. - 22 -

Part Five: Enable, Enhance & Align “The advance of technology is based on making it fit in so that you don’t really even notice it, so it’s part of everyday life.” - Bill Gates If you did us the honor of reading through the first four installments of our thought map series, we talked about four over-arching themes we believe are strategic, 12 discrete sub-segments and referenced over 200 vendors in total. While this is only the tip of the iceberg, we recognize that this is a lot of information to digest, and your head may be spinning trying to make sense of the space and the hundreds of innovative businesses driving change in the land of sales tech today. Rest assured; you are not alone in this sentiment. Technology Enable, Don’t Technology Overwhelm Ask any revenue leader today and I guarantee you – they aren’t asking for more technology. They are trying to make sense of what they have, replace things that aren’t adding measurable value, and build a cohesive tech stack that integrates into the existing workflow of their sellers and enables them, not overwhelms them. We could have easily touched on 50+ sub-segments and over 1,000 companies in this series. If we can leave you with one takeaway from it all, remember this: technology should be an enabler, not the end all be all. This is especially true in the world of sales tech. - 23 -

Salespeople are unique beasts, and we love them for it. They have their idiosyncratic ways of going about their business. They are driven by success, defined as closing business and making sure it sticks. They are compensated accordingly, and they are the lifeblood of any growing company. Enable your sellers, enhance their efforts and eradicate tedious tasks with software-enabled automation. Extend your sales tech stack into existing systems of record to build an integrated backbone that improves the workflow of your team and lets them spend time on the thing that matters most – selling. Technology applied in the most elegant manner should heighten what the awesome human beings in your organization do, and make them better, smarter, and more productive than they already are. Pick any stat you want to out there – the number of tools the average enterprise organization uses for sales technology, marketing technology, customer success; it is an eye-popping number. The key is not to add more dials and knobs to the ever-expanding tech Frankenstack, but rather to leverage software to build a neural network that serves as the cape that your superhero sellers dawn; helping them fly higher, faster, and stronger. Like the CIA, it should do its job by operating in the background, without anyone even knowing it is there. This is not to say that technology is the enemy by any means, or even that there is too much of it out there. Instead, we believe that the best way to deploy technology is as that pure form enabler allowing human beings to reach their full potential. - 24 -

Supplement Your Team With Automation & Improve Outcomes with AI As investors in the innovation economy, it is our job to become deeply entrenched in the categories we invest behind to understand the nuances and the dynamics at play at a granular level, while also being able to zoom out and see the broader trends unfolding over years and years. It is with that lens that we offer a final, hopefully informed, industry perspective to leave you with. The bull market that lasted for over a decade has come to an end. Every company – regardless of industry vertical, end customer focus and GTM strategy – is feeling the pressure to reduce costs and grow efficiently. This means that almost every business out there is cutting headcount and reducing spend, but still needing to see growth to sustain and increase value in the long term. That is a complex algorithm and we’ve seen companies most successfully solve it through the intelligent application and integration of software to improve your organization top to bottom. Most organizations are reducing the number of sales reps or SDRs they have – many are reducing both. And while the market will “rebound” and improve over time, we believe this will be a gradual improvement, not a hockey stick-shaped return to normalcy curve. In reducing headcount, companies are looking to supplement their human efforts with software, driving automation for their teams and improving productivity through the intelligent application of AI and other fast- moving technologies (LLMs and Generative AI). In a world where growth is expected and required, but you have less people to drive that growth, software must be seen as an extension of the folks you still have. Choosing the right technology for your organization, and really understanding the value it provides and how to best glean that value to enable your team is what it’s all about. Hopefully, this thought map series shed some light on some of the newer categories of sales tech software we think are valuable, offered a perspective on why we think so, and provided some indicative vendors to look into to get you started on evaluating these technologies yourself. Choose Your Growth Partner Wisely The investment landscape has experienced growth similar to that of the sales tech arena over the last decade. Hundreds of firms, offering billions of dollars of capital have emerged and expanded and there is more money out there than ever before. All investors are selling money, but be forewarned, it is all not the same shade of green. An investor’s capital loss ratio is the percentage of dollars invested that go to zero. Across 50+ partnerships as a firm, we have only lost money once – our capital loss ratio is just over 1%. The industry average is more than 30x that level – 35.4%. This means that if you take money from an - 25 -

“average” VC investor, you have a greater than one out of three chance that your business goes to zero. That is a SCARY statistic. If you have spent a major part of your adult life building a business, having a binary outcome shouldn’t be palatable to you. It isn’t to us either. The key is to align with a partner that is not just another investor in your “investor stack” but serves as an enabler of achieving a great outcome. In our view, this requires deep domain expertise, sincere passion for your mission, and alignment around a sensible definition of success. This should start with first protecting the tremendous value you’ve created to date, buttressing and bulwarking it, and then building out the city walls from there; never overexposing it to unnecessary risk. You wouldn’t add a piece of software to your tech stack that had a small chance of helping you grow faster, but also had a high probability of torpedoing your entire operation. So, choose your investors wisely, because many will tout logos of companies that have had massive success on their website, but never talk about the dozens and dozens that failed because they were pushed too hard to do unnatural things in the pursuit of unrealistic objectives. At PeakSpan, we look to align with teams that understand how to build resilient, sustainable businesses. We invest in the judgment of our entrepreneurs and understand that pushing companies to do unnatural things by driving them to try to grow faster than they can palpably digest is a recipe for disaster. We see far too many companies get overcapitalized and have venture investors that encourage them to hire at an absurd clip and take their spend posture through the - 26 -

roof to gun for an outlier outcome, knowing all well there is a decent chance the business burns out in the process. We note this not to boast or to claim that we are the best investors on the planet or have worked with the best companies ever built – although to be clear we have worked with tons of amazing teams! Instead, we call this out to elucidate in a statistic that awesome things can happen when you align with a partner who knows your business and category cold, set your sights on a pragmatic set of goals, capitalize the business appropriately, and build value iteratively and incrementally over time. We call ourselves PeakSpan because we believe successful growth company development involves scaling successive “peaks” of value creation, not attempting to sprint up the summit on day one and at the risk of perishing in the process. Closing Thoughts It is impossible to cover any category in a comprehensive way in a piece like this, and that is absolutely the case with sales tech – as we said in the beginning, this is not meant to be an exhaustive review of the ecosystem, but rather a look into the areas we are focusing on and believe are strategic and resilient. We are always learning and believe that it is our job to continue to do so as we strive to be domain experts in this space and others we cover, enabling us to be true thought partners to the teams we work with. Gandhi once said “Live as if you were to die tomorrow. Learn as if you were to live forever.” We love this quote and would love to hear from you with any - 27 -

thoughts, reactions, similar resonant quotes or ideas for improvement with regards to this series. And most importantly, we hope you enjoyed it and gleaned something from it! Lastly, and most importantly, reach out if we can be helpful to you. We got into the business of working with growth-stage companies because we are passionate about helping entrepreneurs. If there is a chance to work together, that’s awesome. But if not, we are huge believers in business karma and just want to be helpful at the end of the day. Put us to the test, and let us prove – through actions, not words – that we can be a great partner in your scaling journey. If you’ve made it this far, thank you for reading! We welcome feedback and are always looking to expand our network of thought partners, so feel free to shoot us a note and let us know what you think! PeakSpan Capital GTM Technology Team Matt Melymuka Co-Founder & Managing Partner – GTM Tech Team Lead [email protected] Andrew Bartusiak Senior Associate [email protected] Charlie Reinkemeyer Analyst [email protected] Mikayla Brenman Analyst [email protected] - 28 -

Sales Technology Thought Map Engagement Product-Led Buyer-Centric Video-Centric Partner Outcomes- Efficiency Enablement Content Productivity Enablement Based Learning * Supernor * mal * * * * Part 1: Value Proposition Articulation Part 3: Strategic Knowledge Flow Part 2: Data-Informed Decision Making Part 4: Optimized Execution Adaptive CPQ & High Velocity Contextual Revenue Renewals Conversational Generative Sales Assist Insights Predictability Automation Intelligence CRM * * * * * * * * * * * Part 5 Enable, Enhance & Align *Denotes company that has been acquired. Rallyware acquired Myagi in May 2023.

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