Kiva Kolstein

The through-line

The recurring idea across everything Kolstein says is that growth comes from designing an environment and a system, then trusting people inside it, rather than from heroics at the point of sale. In the operating context that means enablement, revenue operations and a strategic initiatives team built deliberately ahead of scale [1]. In the leadership context it means the same instinct expressed differently: "you can't micromanage greatness," so the leader's job is to "create an environment where they can grow" and to hold belief in people's potential "many times even before those people believed it in their own potential" [2]. The second recurring theme is preparation as a discipline. Whether it is a two-week onboarding, a sales call, a conversation with a stepchild or a market entry, his position is that nothing important should be improvised: "I never show up and wing it ever" [2], and "you can't Wing training you can't make it up on the Fly" [10].

What has shifted is scope. Earlier he talks in the vocabulary of the individual seller, the ramp, the deal and the hire [10]. Later the same convictions are expressed as organisational architecture, integration strategy after acquisitions, and culture that other people have to carry when the leader no longer can [1][2].

On operational excellence as the growth engine

Growth starts, in his framing, with a go-to-market strategy that makes sense to the customer: pricing, packaging and customer segmentation built around specific verticals, subverticals and personas, with sellers trained "to speak the language of the customer" and the platform positioned as purpose-built for that persona [1]. That was not how things began. When he arrived, AlphaSense was at "13.9 million in ARR" with a small team "selling Alpha sense generically," pitching a pharmaceutical company, a hedge fund, a bank and an energy company the same way and "hoping that the smart person sitting on the other side would recognize the value" [1]. The correction was a persona-based sales approach, training sellers to sell to a strategy executive versus corporate development versus investor relations, and to a hedge fund versus private equity [1]. The company today serves just over 4,000 enterprise customers split roughly evenly between financial services and the corporate and consulting side [1].

A third structural piece, alongside enablement and RevOps, is a strategic initiatives team. His observation is that in most companies, including AlphaSense six or seven years earlier, the executive leadership team is the body charged with finding new markets, new personas and new products, and that this "dilutes or distracts the elt" [1]. The dedicated team exists to incubate ideas, experiment in a subset of the market, launch broadly if it works and kill it if it does not [1]. How much evidence is enough before committing is deliberately unfixed: "the amount of data that gives us the confidence it will work or it won't" [1]. Opening the first office in Singapore took three months of investigation before the decision [1]. He is also candid that demand was never the constraint: AlphaSense is "an amazing product in a competitive landscape that doesn't include a lot of innovation," and the hardest thing over seven years was building the team fast enough to get in front of the people who wanted it [1].

On sales enablement as a secret weapon

Enablement is the function he names first when asked what drove growth, and he calls it "a secret weapon" in a fast-growing, complex organisation, involved at every stage from onboarding through to equipping sellers with the tools, training, content, technology and analytics to engage buyers and close [1]. The trigger for building it was practical: the persona-based approach demanded more training than the existing team could deliver at the pace they were hiring [1]. He describes onboarding as "Navy SEAL style" [1], and in more tactical terms as the first two weeks in early and staying late, hour-by-hour sessions all day, homework at night delivered back the next morning, certification on things like objection handling and the product where possible, with the aim of getting the new hire somewhat productive by week three, "which is when ramp really begins" [10]. World-class enablement and what to expect of a seller during ramp is a subject he has taken up elsewhere as well [3].

He is unusually insistent that ramp is a modelling problem, not just a coaching one. If you get ramp wrong, if you expect double output in month four, "all of your numbers are wrong," because the figures given to the board are built on where each seller sits against their ramp curve multiplied by expected production [10]. Accelerating ramp then loops back to enablement: what does this seller need in month three, month five, month seven to be productive [10]. Defining the KPIs to watch over the first six months matters because "you want to hire quickly but also you want to let people go quickly that aren't going to work out" [10]. Investing time in new hires is a theme he has returned to in discussing the move from individual contributor to management [8].

On RevOps and telling a story with the data

RevOps is his second named secret weapon, described as "the connective tissue across all of customer success and sales and marketing" [1]. It measures every facet of the business from the top of the funnel through closed deals, renewals and upsells, and slices the data by rep, by rep tenure, by manager, by AE and SDR pairing, by geography, vertical, subvertical and persona [1]. That data goes not only to him but to every revenue leader, and it informs "every single decision that we make": where to double down, where to pull back, which territory or vertical to open [1]. He is explicit that the team's remit is not only measurement but narrative, helping him tell a story with the data in company-wide presentations, to the executive leadership team and to the board [1][4][6]. The third function is human intelligence: because RevOps is closely connected to revenue leadership, it acts as his "eyes and ears" on how the team is reacting to a new spiff, a new comp plan, a rejiggered territory, a new market or a new product, delivered as an email every Sunday night [1]. Underneath all of this sits his view that a revenue team is constantly changing and the go-to-market motion cannot be expected to stay static through that change [5].

On hiring sellers and spotting grit

Hiring starts with the product, not the résumé: what you are selling, at what price, over what cycle length, because "the profile of the seller changes depending on the product that you're selling" [10]. He draws a sharp distinction between two enterprise sellers who look identical on paper, both having sold to the largest companies in the world and both having exceeded targets, where one expects to close on almost every client meeting and the other knows how to "weave your way through the hierarchy of really complex companies building influence building advocacy building a business case" [10]. Most organisations need both, and sequencing is a funding question: hire the more transactional seller closing smaller deals first, because that revenue funds the seller running six- or nine-month cycles on much larger ones [10].

Beyond raw intelligence, intellectual capacity and past performance, the differentiator he names is grit, "the greatest or the fastest or best predictor of future success" and also the hardest trait to identify [10]. He offers two diagnostics for reading past success. The first is whether the candidate "sell gold in a gold rush," succeeding because the product was easy to sell [10]. The second he borrows from Rocky 3, where Mickey tells Rocky that the worst thing that can happen to a fighter had happened to him, "you got civilized," and Kolstein applies it directly: the worst thing that can happen to a successful enterprise seller is to get civilized, so the leader's job is to work out whether this person is still willing to roll up their sleeves [10].

At AlphaSense the profiles are split between account executives who sell new logos and expand inside existing accounts, customer success who cultivate and renew, and product specialists who convert trialists and drive adoption into daily workflow [1]. The filter is who has sold to knowledge professionals or managed relationships with Fortune 500 and Fortune 1000 companies, then one level deeper, who can speak the language of a hedge fund analyst or a pharmaceutical investor relations professional, and whether that language can be trained if they arrive without it [1].

On pipeline, SDRs and the minor leagues

The decision that the highest and best use of an account executive is time in front of customers and prospects, not self-generated cold calling, led to a sales development organisation of about 150 people paired with AEs at close to a one-to-one ratio [1]. It produces 35 to 40 percent of pipeline, making it the most consistent generator, with the remainder coming from AEs, who carry their own generation target, from account managers finding new pockets of opportunity inside client firms and handing them to AEs, and from marketing [1]. The second payoff is talent: the SDR team is "an incredible minor leagues," and the wider organisation is full of SDR promotes who moved into AE, account management, product, content and marketing roles [1].

On working the prospect universe, he calls prioritisation the first thing a sales organisation must do, since you want to reach the buyers likeliest to buy first, which makes pattern recognition across sectors and geographies essential [10]. He also advocates creative cuts, such as organising prospects by their fiscal calendar so you are always selling into someone's fourth quarter, when buying tends to concentrate [10]. Asked whether to chase low-hanging fruit or long-cycle deals, his answer is both simultaneously [10].

On choreographing the sale

His most distinctive tactical belief is that "a successful seller should choreograph the entire experience" [10]. He argues against the intuition that memorisation kills creativity: if you have memorised the pitch, the deck, the demo and what you want to say about your company, you are freed up to be in the moment and have a real dialogue instead of thinking about what comes next [10]. Choreography extends that logic to every touch, on the premise that every single interaction with a prospect can move a deal positively or negatively. He walks through it concretely: what you and your colleague do in the hotel lobby that morning, how you assign parts and decide who answers which question, whether you read the annual report on the table in the client's lobby and which part of the 10-K you mine, what you ask the receptionist, what you glean from the assistant on the elevator, what you do if the person you are meeting asks you to describe your company in the elevator when five others are waiting upstairs, whether you walk to the coffee machine with them, and what you ask when the technology fails [10]. The same applies to the first call and the first voicemail [10].

Complex enterprise selling he compares to running for office: you spend enormous time meeting people in the hope they support you later [10]. Since few people actually make the buying decision, the work along the way is building influence and advocacy, getting people to stand up for you when the decision-maker asks their advice, while assembling the business case, because the decision ultimately turns on whether the value exceeds the cost [10]. It begins with mapping the organisation to understand the path to close, done alongside the SDR and sales operations [10]. On tooling he is deliberately unsentimental, saying with respect to everyone selling software to sales organisations that it is not that important, and naming LinkedIn and LinkedIn Navigator, Salesforce, Boomerang for timed sending and Tout App for email tracking [10].

On building leaders, not just teams

He traces his leadership philosophy directly to parenting, which he says changed how he thinks about leadership "in a way that my career never could" [2][7]. Children are not listening to what you say, they are watching what you do, how you handle frustration, how you walk in the door after a hard day, whether you are present or distracted, and "there's no hiding at home," which keeps you honest in a way that an office does not, because in front of a room "you can project confidence even when you don't feel it" [2]. As children get older the job moves from protecting them physically to preparing them emotionally, building resilience, confidence, the ability to make decisions, advocate for themselves, own mistakes and recover [2]. The transfer to business is direct: you cannot script the outcome or force belief, all you can do is create an environment that is clear, that has consistency, that holds everyone to a standard [2]. Parenting also taught patience, because "growth doesn't happen on your timeline" and you have to meet people where they are, seeing potential before they see it and holding the belief while you trust the process [2]. What he says he cares about is "building leaders uh not just teams," helping people stretch far beyond what they think they are capable of, and how people hold themselves and each other accountable [2][7].

Stepparenting sharpened the point about intentionality. Two of his three children are stepchildren who were ten and seven when he met them twelve years ago, so he had to work out how to insert himself into their lives as parent, friend, uncle and partner at once [2]. That produced a habit of thinking carefully about every interaction and preparing alongside his wife on who plays what role in a given conversation, more deliberately than with his biological son [2]. The lesson he carries into leadership is being "hyper intentional, hyper deliberate" [2].

On leading as yourself

The inflection point he returns to is his first day as a head of sales [2][7]. Wanting to prove he belonged, he spent the prior week building a thirty-slide deck stuffed with quotes from business journals, frameworks from leadership books, case studies and vision statements drawn from leaders in business and sport, every slide smart and polished [2]. He delivered it in a darkened room to the whole sales organisation and felt good about it. The CEO's response is the part he says he will never forget: those were great stories from great leaders, but "we didn't hire any of the leaders that you quoted in your deck. We hired you. I want to know who you are, how you lead, why all these sellers should follow you" [2]. It stung on day one, hour one, and he says the CEO was exactly right [2]. The related questions of how a cohesive leadership team should function, and how to judge whether a company is a genuine fit for your skills, are ones he has addressed in discussing the path from individual contributor to management [8].

On acquisitions and letting the best idea win

AlphaSense has been through four acquisitions in four or five years, most recently adding nearly 150,000 expert transcribed calls across public and private companies [1][2]. His single piece of advice to another CRO contemplating one is to be open to the acquired company's ideas and work out how to incorporate them: "let the best ideas win" [2]. The questions he asks each time, whether the target is a five-person company or a much larger one, are how to take the joint product to market, how to retain all the acquired talent, and how to turn one plus one into three [2]. Rather than forcing the acquired team into what you have built, however good you believe it is, the work is identifying what is fantastic about their culture, product, go-to-market strategy, pricing or commission rate and folding it in [2]. The stated goal is that the acquired company never feels acquired, but instead feels immediately like part of a bigger, better AlphaSense, which requires coming with a plan covering people, systems, technology and go-to-market together [2].

This connects to a broader principle: "debating ideas, not people" [2]. Inside an existing organisation the best ideas can come from anywhere, from a junior SDR who just started to the CEO, and if the organisation is willing to debate the idea rather than the person and let the best one win, good things happen [2]. The condition he attaches is evidence: come with data and a decision matrix that lets everyone see the upside, downside and opportunity, and your idea gets evaluated against anyone else's [2].

On culture and feedback

He is direct that his personal influence over culture was greatest early and has necessarily diluted as headcount and geographies grew, which made hiring people to carry the torch a central task [1]. The culture he describes is collaboration, best-practice sharing, alignment against a business goal and driving hard at it, lifting each other up and recognising that everyone is there to grow the business regardless of function, visible in people cheering for each other, jumping into rooms to role-play, and staying late to work on objection handling or negotiation [1]. It is set in the first three weeks of onboarding, which lay out what is expected of you and what you can expect in return [1].

Two further attributes define it. The first is that it is feedback-rich, with feedback given in the moment, so the people who thrive are open to receiving it and good at giving it, and that has to run in both directions: he says there is hardly a meeting or presentation of his where someone on the ground does not tell him afterwards what he could have done differently or how a word or two might have landed better [1]. The second is a seat at the table, hiring smart, capable, sophisticated people who are expected to arrive with fresh eyes and a new perspective and to use it [1]. The upward mobility of the SDR pipeline is the practical proof of the culture rather than a separate policy [1].

On the two-hat job

Asked how he divides time between president and chief revenue officer, his answer is that he does not think about it much, because both roles resolve to the same objective [1]. As CRO he runs sales, service, RevOps, enablement and the supporting functions of the revenue organisation; as president he works across the executive leadership team to align marketing, content, product, finance and strategic initiatives against the same goal [1]. Designing pricing, packaging, customer segmentation, verticalisation and entry into new markets sits in both, so "the two roles to some extent blend" [1].

Takeaways

• Build sales enablement and RevOps before you think you need them; at AlphaSense neither existed at $13.9 million in ARR, and both became what he calls secret weapons behind seven years of growth [1].
• Stop selling generically. Train sellers on the language of a specific persona in a specific subvertical rather than demoing the product and hoping the buyer connects the dots [1].
• Give RevOps three jobs: slice every metric by rep, tenure, manager, pairing, geography and persona; help leadership tell a story with the data; and act as eyes and ears on how the field is reacting [1][4].
• Get ramp expectations right before trying to accelerate ramp, because board numbers are built on where each seller sits against that curve [10].
• Hire for grit, and stress-test past success by asking whether the candidate sold gold in a gold rush or has simply "got civilized" [10].
• Choreograph every touch in a deal, from the hotel lobby to the annual report in reception to what you say in the elevator, because each interaction can move the outcome [10].
• In complex enterprise deals, build influence and advocacy across the organisation while assembling the ROI case for the one person with authority to buy [10].
• After an acquisition, take the best of the acquired company's culture, pricing, product and go-to-market rather than imposing your own, and let the best ideas win [2].
• Lead by creating a clear, consistent environment with a standard, and hold belief in people's potential before they hold it themselves; you cannot micromanage greatness [2].