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Strategic Communications Advisory For Visionary Founders
39 HR Tech Founders
GTM Lessons
Productize Legacy Manual Processes to Own the Category
Marcelo found that productizing outdated manual services created category-defining differentiation impossible for competitors to match. “The companies operating in this space, they used to operate in such old fashioned, manual, outdated way that once we showed up and started building things that creating a product out of a service in the employment space and payment space…it felt like a different market altogether because you couldn’t even compare our solution to what existed.” Customer feedback confirmed the gap: “there’s honestly nothing like this.” The iPhone comparison was deliberate—when Remote launched software for global employment that had been handled manually for 20+ years, “it felt a bit like…after the first iPhone came about. Then there was the iPhone and everything else.” This level of differentiation made traditional competitive positioning irrelevant because prospects couldn’t even compare the solutions side-by-side.
Early Customers Should Co-Build Product, Not Maximize Revenue
Tomer optimized early customer acquisition for product development, not revenue. “Step one was getting that initial set of customers that really understand your goal with them, and that your go to market is less about let’s make as much money as you can…the goal is to finding the right customers to help develop a great product.” He applied two strict criteria for early customers: they needed to “align with kind of your long term customer direction” and “these are people who are really good in the feedback…their personality is the type of person that will tell you what they think for real and they’re easily accessible.” At Gusto, “every single customer talked with me, like probably every day. And we kind of co built the company, the products together.” This phase stayed invite-only until they had validated product direction with the right customer set, then opened the funnel.
Find Buyers Too Stretched to Build In-House
Jason went after 50-300 employee tech companies with “a people ops team of about one” who were “really stretched.” The constraint wasn’t a bug, it was the feature. These teams “want to bring DEI training, they want to bring manager training, they want to bring employee experiences to their team, but they’re a team of one.” Being overwhelmed created pull: “to outsource to a platform like ours was incredibly helpful.” The bonus was velocity: “they move quickly. They’re not the large enterprises where procurement teams and other teams may slow down the people ops team.” One overwhelmed buyer beats ten comfortable ones. — Jason Lavendar
Narrow Your ICP More Than Feels Comfortable. Industry-Specific Beats Broadly-Defined Enterprise.
René was operating in a $400 billion market, which made the instinct to stay broad feel rational. He pushed back on it anyway. His advice to any founder selling into enterprise was direct: “pick an industry, pick a market, define enterprise more narrowly, understand what keeps them awake at night, and if you can fix that, then you can scale it.” The logic behind the sequencing was grounded in what he’d seen go wrong with broad targeting: “with enough marketing you can ultimately sell anything, but the unit economics aren’t always going to make the sense that you want them to make sense.” A deeply solved problem for one specific buyer type in one specific context was what created the proof points and economics to expand from — not the other way around.
Straddle Budget Categories to Expand TAM
Jaclyn anchors Benapass in “the benefits market” because “you have to think of your market within the confines of a certain budget or line item for companies if you’re going to have customers.” That’s a massive category: “30% of total compensation is spent on benefits and that sums for about $4 trillion” in the US alone. But she also describes the product as “benefits infrastructure” and “financial infrastructure” that solves problems around “currencies and time zones” for global teams. This dual framing lets her sell into HR and benefits teams while also opening conversations with finance and operations buyers who control infrastructure spend.
Build Community Around the Job, Not the Product
Andres didn’t create a Fetcher user group—he built “a community that’s around recruiting in general” where members discuss broader problems beyond sourcing. People share “not only things that they’re doing on around sourcing, but also how are they automating other areas, what areas that they really care about.” Topics ranged from diversity hiring to automation strategies across the recruiting function. The webinars eventually drew “over a thousand people” because the content addressed their role’s challenges, not just product features. This approach turned community members into category evangelists who understood the broader transformation, not just one tool.
Target Pain Intensity Over Market Size
Prem ignored the entire recruiting market and zeroed in on “high volume entry level roles where there’s pain points around having to do seven phone screens a day and write seven sets of follow up emails and take seven sets of notes.” The specificity wasn’t about the role type, it was about the repetitive manual work that created urgency. He wasn’t solving for all recruiters, he was solving for recruiters drowning in volume who needed relief immediately. The pain of doing seven identical tasks daily beats the appeal of a massive TAM every time.
Don't Move Upmarket Just Because Investors Want You To
Sid kept Wizehire focused on “Main street” despite investor pressure because moving enterprise meant “the feature requirements, your product strategy has to change because their user is going to change.” He watched “a lot of false starts with some companies where they will go from SMB land, go up mid market or go up too quickly” and realized the shift wasn’t just about deal size. With franchises, “it is the same problem, the same challenge” as single-location businesses, so “we get to work with someone from their first higher to their hundredth higher.” The product roadmap stayed coherent because the user remained consistent, not because enterprise deals looked better on a pitch deck.
Position Within Adjacent Category While Building New One
Ben positioned BrightHire “in the broad sense in an existing category, right. Video interviewing is something that folks have done for a long time, but the category itself has transformed quite a bit” while declaring “the subcategory interview intelligence is new. We are the leader.” This dual positioning solved the education problem: buyers understood video interviewing but needed to learn why intelligence mattered. He wasn’t asking prospects to believe in a completely foreign concept, just an evolution of something they already knew. The familiar anchor gave sales conversations a starting point before explaining the differentiation.
Turn Compliance Hell Into Your Competitive Moat
Kevin’s first hire was “a lawyer” which “completely flabbergasted my investors” but the investment paid off. Building against ERISA regulations meant “it took us a year and a half” before launching with customers, and they “joke all the time. Had we known how much regulation there actually was, we probably would never have started this company.” The upfront pain created an unexpected advantage: “we ended up building this large moat that we didn’t know were building, but it became a moat for us.” Competitors “have to outsource all this work and we have built this all internally which allows us to have this unique business model.” The regulatory complexity that almost killed them became the barrier that kept others out.
Kill Buyer Fear With Data, Not Reassurance
Dirk faced buyers who believed “suddenly, once you offer paid parental leave, everybody’s going to go out and have a kid” or worried “if I also leave, they’re just going to quit.” Rather than dismissing these concerns, he addressed them directly with specifics: “you do see an uptick in birth rate versus historical rates, but you’re not going to suddenly see everybody out.” He reframed the quit narrative with data showing people leave “not because they want to, but because usually the company is not supportive enough.” The misconceptions weren’t irrational, they were data gaps. Filling those gaps early in conversations moved deals forward faster than any feature pitch could.
Build Frameworks That Position Your Product as the Solution
Hanns spent six years in consulting “interacting with and engaging with lots of different HR consultancies” including “big four HR consultancies” and “very kind of boutique consultancies in the HR space and basically aggregating all that knowledge from them.” This allowed him to develop frameworks like the maturity model showing progression through skills-driven organization stages. These frameworks weren’t just educational content—they established the category logic that made Cobrainer the natural answer. When he finally launched the SaaS product, buyers already understood the discipline because he’d codified it through years of consulting work, making the product an obvious fit.
Position Against the Job, Not the Incumbent's Features
Anthony built sophisticated payments infrastructure and tax engines but realized “customers don’t really care about that.” Instead, he repositioned by asking “what are the competitive alternatives and where do we fit into somebody’s life and in their context?” Rather than comparing features against ADP or Paychecks, he positioned against “traditional w two payroll systems or accounts payable systems” as categories that “weren’t purpose built for this specific industry or this specific use case.” The shift wasn’t about being better at payroll—it was about solving a fundamentally different job that existing categories couldn’t address. Buyers don’t evaluate you against features, they evaluate you against the alternative way they’re solving the problem today.
Bet on PR Early, Even If It Hurts
Within the first six months, Jared hired a PR firm where “the monthly fee was more than our mortgage payment” which forced a decision moment with his co-founder. They looked at each other and said “hey, I think this is worth it. We could do it. It’s going to get our name out there. It’s going to get the people to know that we’re serious and who we are.” The investment paid off long-term: they “still use them today” years later because the firm understood their message and eliminated the need to “reeducate” new partners. The painful early bet on professional PR created compounding returns that bootstrapped marketing couldn’t match. – Jared Pope
Define Your Category Term When Existing Ones Don't Fit
Mike “stood up this term of hiring intelligence because we didn’t think there was good definition for what we’re doing” even though he acknowledged “these things kind of just take their shape and it’s oftentimes challenging.” Rather than forcing fit into talent analytics or talent intelligence, he created new language because “we don’t think anybody else in the world is doing this and the ways we are.” The decision wasn’t about being contrarian—existing categories described adjacent problems but missed the core value proposition. When no category captures what you actually do, own a new term rather than confuse buyers by wedging into the wrong bucket.
Bottoms-Up Wins When Hiring Managers Are Your Champions
Siadhal shifted from top-down sales after discovering that stated buyer preferences didn’t match actual decision-making. “We’d have a bunch of success criteria, let’s say for a POC, the success criteria would be all around things that the senior leader, the buyer had told us were important to them. But then when you sort of, that was almost like their stated preferences. But the reality was when it came to them making decision is they would just survey the people who use the product.” In hiring specifically, the math favored end users: “The aggregate weight of that voice is a lot larger than the buyer. Some of these hiring managers are VPs of engineering, VPs of sales, whatever it might be. Some of these hiring managers are CEOs.” The bottoms-up motion worked because “what became possible was actually something that primarily delighted the end user,” making it natural to build the go-to-market motion around the land with end users rather than fighting uphill against their collective authority.
Solve Business Problems, Not Just HR Problems
Barb coached her team to avoid CHROs who only wanted to “do business with themselves”—HR’s pattern of buying tools that solve internal operations rather than company-level problems. “HR is quite famous for doing business with itself. They’ve spent a truckload of money on HR tech, a huge amount of VC money has gone into that. And at the end of the day, you got to be really honest and say, are we solving a really meaningful business problem? It can’t just be solving HR problems.” She pushed her team to qualify for executives who wanted meaningful business impact: “What’s it going to take for them to be maybe not promoted if they’re at the top of the rank, but at least really call out for having a meaningful impact on the business.” This meant targeting CHROs solving for diversity, brand strength, efficiency, and turnover—metrics that mattered to the CEO and board—rather than just streamlining recruiting operations.
Target Next-Gen Buyers Who Believe in Change
Michael refused to waste time on legacy L&D leaders who couldn’t envision alternatives to decades-old methods. “We really only work with learning leaders that are very innovative, and usually that’s learning leaders within a business unit.” The qualification was binary: “You have to believe in this for it to work. We can show you all the data of like, hey, this is going to drive way more satisfaction, way more engagement, et cetera. But if you don’t believe in the idea of modernizing learning and there being an alternative to what you’ve been doing for the past 30 years, then it’s going to be impossible for us to work with you.” This led them to target sales teams first, where innovative leaders would see success and then pressure central L&D to adopt: “Oftentimes we’ll start by working with the sales team and helping upskill the sales team. The sales team always sees a lot of success with it. And then from there, they essentially go to the L and D team and say, hey, why are you not using this?”
Post Customer Wins, Not Product Features, on LinkedIn
John’s organic social strategy focused on customer outcomes rather than product capabilities. “We create content around how these really fast growing companies make really critical hires. We post about success stories” instead of feature announcements or capability explainers. This approach generated inbound demo requests because prospects could visualize their own success through pattern matching with similar companies. The strategy worked as part of their three-channel growth engine: “Inbound, we do a lot of organic social, mainly posting on LinkedIn. So we create content around how these really fast growing companies make really critical hires. We post about success stories and just share content and that leads to people being interested and booking a demo to post on our platform.” — John Kim
Start Investing in Thought Leadership Early
Karoli built outsized credibility as a Series A company by positioning Jobbatical in high-level policy conversations about immigration and economic growth, not just HR tech discussions. “The impact or the thought leadership we have managed to build through media, through events…bringing the discussion of immigration visas, you know, how we need to enable international hiring in order to grow the economy. So we really have managed to kind of build ourselves as thought leaders and be part of the conversations on a very high level with top tier media.” This included securing the main TED stage “just before we did our series A” to discuss borderless talent—something that “doesn’t happen very often at the early stage.” By framing their solution within macro trends (300 million annual moves, immigration modernization), they earned credibility disproportionate to company size and created pull from enterprise buyers who wanted to be part of the category shift.
Dam Demand from Adjacent Categories Rather Than Building New One
Jennifer avoided the expensive work of building a new category by entering through existing pain points in adjacent categories. “We often come in through one of the jobs to be done of things like my pulse scores came back and they’re really bad. I need help moving them or I no longer have an off site budget. How do I still keep my team connected?” Rather than educating buyers on “team performance platforms,” she let them search for learning and development, team engagement measurement, or team building solutions, then explained “our offering is actually better than the other alternatives out there.” The positioning worked because it complemented rather than replaced: “We’re not trying to say, you know, you never want to hire a coach or facilitator. It’s just that oftentimes you can only afford that for so many people in your organization. And if you want to give something to everybody in the company, you need something more scalable.”
Kill Digital Outbound, Win With In-Person for Enterprise
Charlotte shut down all traditional digital channels after realizing they’d stopped working for enterprise sales. “At the beginning of this year we’re like, this isn’t working. We’re not getting any type of conversion. We’re spinning our wheels. We’ve set up this whole cold calling and all this different stuff and none of it’s really yielding anything.” The replacement strategy: physical presence and relationship building. “We are just showing up in person to our events, to other people’s events, and really making connections and hosting like dinners before a big conference the next day where we know a lot of people will be there, those two things have completely driven our top of funnel strategy.” The shift was so effective they “pretty much turned off everything else” and eventually had to pause the new approach because they “didn’t have enough time to take all the meetings.”
Test Your Pitch in Seven Seconds or Less
Sloane learned that unclear positioning burned critical fundraising cycles and damaged investor relationships. “I think my struggle was early on when we were kind of really figuring out exactly what our narrative and our lane and our positioning was, which is a natural part of the process. But it does burn cycles and if you’re burning them with investors that are potentially going to invest in your round it can actually be strategically damaging.” The fix: brutal simplicity. “You have to have a narrative that is easy to understand and that can be explained in probably seven seconds.” If you couldn’t articulate your thesis that fast, you weren’t ready to fundraise—and every minute spent explaining a fuzzy story to potential investors meant wasted relationships that couldn’t be recovered later in the round.
Category Creation Confuses Enterprise Buyers — Use Their Existing Language
Nitzan tried creating a new category for their two-in-one solution that replaced two existing layers in the industry. “No one will buy. I mean, a few, but very few bought it because it was very tough for them to understand because that’s not how they used to buy.” HR professionals had “a very busy job and they’re doing a lot of work that is not about figuring out what this vendor is doing.” The fix: abandon category creation and use existing language. “We separated our whole marketing proposition to actually those two layers that we replaced and say, you can buy it for this layer or buy it for that layer, and of course, you can buy for both, but only when we change it to actually name the layers as they used to be, they started to say, oh, now I understand.” RFP invitations followed immediately because buyers finally understood how to purchase within their existing procurement frameworks.
Build Buyer Purchasing Criteria Framework From Win-Loss Data
Tony installed a systematic framework to iterate positioning strategically, not just tactically. “On every deal we lose or we win, we understand what the buyer wanted to see and why they selected us or why they did not select us as a vendor. And iterate on that we keep adding more buyer purchasing criteria, changing them, monitoring them, see how it’s evolving.” This went beyond A/B testing homepages or tweaking sales decks—it created a living dataset of what actually mattered in buyer decisions. The framework tracked both reactive criteria (network reach, software experience, pricing) and proactive criteria they introduced: “How much do we help you become more employee centric? Are you picking us because we are employee centric or not? So this is not necessarily they’re looking for this, but this is something that we’ve added because we believe it’s important.” This systematic capture enabled Oyster to shape buyer preferences while iterating positioning based on actual purchase behavior.
When Selling Into Risk-Averse Enterprises, Find The Internal Innovation Unit
Ron didn’t try to sell into the core of New York Life. Instead, he found New York Life Ventures, the team inside the carrier chartered to incubate new ideas and make strategic bets. He recognized that slow-moving industries like life insurance had a structural reason for their risk aversion: “more than any other vertical, these guys are supposed to weather the storm no matter what.” Rather than fighting that culture, he routed around it. “Many of them have these tiger teams that are trying to incubate new business ideas. And that was the case with our first life insurance carrier.” The goal wasn’t just to close a deal but to give that team a reason to champion Empathy internally: “we try to make sure that they have a competitive advantage if they work with us.”
In Enterprise Sales, Intangible Assets Like Brand And Domain Name Compound Faster Than Most Founders Expect
Aaron spent over half a million dollars on the alex.com domain at a stage where most founders would have that money allocated elsewhere. The rationale was grounded in enterprise sales mechanics, not vanity: “in enterprise sales, intangible assets more matter a lot. And so things that you can differentiate on the branding side, you know, is very important.” The previous name, Priora, was “kind of a mouthful and it’s hard to pronounce, it’s hard to share, it’s hard to refer people to” — a distribution problem disguised as a branding problem. The rename produced a direct, measurable lift: “we’ve just seen a huge increase in word of mouth and inbound.” And with enterprise contract sizes in the mix, Aaron’s view was simple: “it’s an asset” and “it’s certainly has paid off immensely already in the past several months we’ve had it.”
Your Real Competitor Is Often The Status Quo, Not Another Vendor. Build Your GTM Around That.
Deborah didn’t position Sparrow against other software companies because there weren’t any worth positioning against. Her framing was blunt: “our biggest competitor is someone managing this in house who wishes they were not managing this in house.” That single insight shaped the entire sales motion. Instead of running competitive displacement plays, the pitch was built around the cost of inaction: compliance risk, payroll errors, retention loss, and tens of thousands of dollars spent on employment lawyers every time someone went out on leave. Senior buyers got it immediately. As Deborah noted, “chief people officers, CFOs get it right away. Lawyers usually get it right away” — because they were the ones living inside the problem and already knew the in-house approach wasn’t working.
Learn To Distinguish Product-Market Fit Pain From Execution Pain. They Require Opposite Responses.
David named this the single most important thing he’d tell his earlier self: “knowing how to interpret pain. Doing a startup inevitably is hard. You are inevitably going to feel pain and being good at discerning that — is that a signal that means I don’t have product market fit, that this isn’t the right offering, that I need to shift, I need to adjust? Or is this pain just because startups are hard?” The filter he used was vision congruence. When VC or market feedback aligned with his view of where the world was going but criticized how he was executing or telling the story, he adjusted. When the feedback contradicted the vision itself, “I ignored those people.” For prospects specifically, his approach was different: “I think you need to share your vision of the future and then listen very closely to the feedback you get from the market. Because I think being iterative and agile to that feedback is a gift.”
In-Person Effort At Critical Deal Moments Closes Deals That Zoom Calls Lose.
Will applied this principle across two distinct sales motions: closing investors and closing competitive recruiting situations. On the recruiting side, he had three candidates simultaneously fielding multiple offers from competing companies. He took each one to dinner, and in one case rerouted a flight to meet a candidate face-to-face in Atlanta who had nearly made up his mind elsewhere. All three accepted. His explanation was direct: “when you’re an entrepreneur you’re constantly trying to defy the odds the odds are against you in every direction and you’ve got to find just basic things that work.” The same logic applied to investor negotiations — he pushed for an in-person meeting to hold his ground on deal terms, and the investor’s response after hearing him out face-to-face was telling: “I just wanted to see that you like how you were thinking about it and I could see that you’re serious and I like founders that know what they want.” In a remote-default world, Will’s view was that showing up in person had become a differentiator: “there’s an energy there that you’re able to harness and tap into and it’s very human to just have that in-person connection.”
Leading With Disruption Messaging Can Kill Deals. Start With The Problem They've Already Named.
Confirm’s early enterprise motion was built around telling HR leaders that performance reviews were broken. It went nowhere. David’s summary of what happened was direct: “if you tell people that what they’re doing is wrong, then they’ll say pound sand.” The fix was to start with discovery — ask what they’re trying to solve, then inject only the parts of the solution that map to problems they’ve already surfaced themselves. His rule on the rest: “if you have a solution to a problem they have not surfaced, don’t pretend that they have that problem.” Instead, he’d introduce it sideways: share what similar companies at their size and stage had reported, then ask if they recognized it. “If they say no, don’t fight it.” That reframe — from evangelist to diagnostician — was the single biggest change to their sales motion.
Feedback Loops At The Customer Level Are Both A Retention Tool And A GTM Signal
Tom built a simple but revealing system at Hone: learner feedback collected one month after each class got piped directly into a Slack channel the whole team could read. What came back wasn’t just satisfaction data. Customers were reporting outcomes Tom hadn’t pitched – “it’s helped with my communication with my spouse because being a great communicator or maybe conflict resolution is a useful skill as well at home.” That’s a whole-person value proposition surfacing organically from the product, not from the marketing team. Tom stayed close to it deliberately: “whenever I take one of our classes it’s just so transformational that it reminds me of this impact that we’re having.” The practical GTM move here was treating delayed feedback as a signal about the real job the product was being hired to do, not just a metric to report to the board. When customers start describing benefits you never promised, you haven’t just found a retention story – you’ve found a positioning angle your competitors almost certainly aren’t using.
Underpricing Early Destroys More Value Than You Realize. Raise Prices Before It Becomes Painful.
Figures launched at 400 euros per year, and when they turned the spreadsheet into a product, Virgile lowered the price further — reasoning that a cheaper barrier to entry would fuel the data co-op and attract more customers faster. He later called it “one of the biggest mistakes” he made. When he raised prices 3x in June 2021, the market didn’t flinch: “it didn’t impact at all our win rate at the time.” The damage wasn’t in lost deals. It was in the renewal cycle his first salesperson walked into — converting legacy customers from 400 euros to 2,500 euros. “Those first hundred or so customers have been a nightmare to renew.” Virgile’s summary of what went wrong was blunt: “I devalued the value of our product.”
Enterprise Buyers Aren't Evaluating Your Product. They're Evaluating Their Career Risk.
Wagestream integrates directly with payroll and workforce management systems — which meant a failed implementation wasn’t just an operational problem, it was a career-defining mistake for whoever signed off on it. Peter described exactly what was running through buyers’ heads during the sales process: “who else is doing this, will I be fired if I buy this?” That question wasn’t background noise. It was the actual sales object. The entire early GTM motion had to be designed around answering it — building a reference customer base, establishing social proof, and giving buyers something to point to internally if the decision was ever scrutinized. When your product touches critical infrastructure inside a large organization, the person across the table isn’t buying software. They’re buying protection from a career risk they can already see.
The CFO Has Always Been A Stakeholder In People Operations Decisions. Make Their Value Proposition Explicit Early.
Even in ChartHop’s earliest five pilot customers, Ian noted that “three of them were the sort of CFO or finance leader being sort of the core person I was working with or at least one of the core stakeholders.” The reason was simple and structural: “people for most companies are their biggest cost.” What shifted over time wasn’t the CFO’s involvement — it was market pressure making that involvement impossible to ignore. “In this market where CFOs are really being tasked to evaluate line by line every bit of spend that is happening, we want to make sure that our value proposition to the finance buyer is just really really crystal clear.” Ian’s approach was to maintain that clarity regardless of who initiated the conversation: “while the people operations leader is usually the person buying our software, it’s a good chunk of times it is a finance or operations that’s making the purchase.”
Category Creation And Category Disruption Can Coexist In The Same Product - And You Have To Be Able To Explain Both
Hanna ran two fundamentally different GTM conversations simultaneously at Localyze, and she was clear-eyed about what each one required. On the disruption side, Localyze was going head-to-head against immigration law firms and relocation agencies – replacing them outright. On the creation side, she was building something that had no direct predecessor: a consumerized mobility platform with housing partnerships, marketplace components, and buddy systems for employees moving abroad. When asked how she categorized the company, she didn’t collapse the two into one tidy answer: “I would say it’s a mix of both.” The practical consequence of holding both frames was that the HR buyer conversation about replacing a law firm – grounded in workflow, case visibility, and inbox chaos – was a completely different sale than the conversation about a new platform category built around the idea that “in the careers nowadays it’s very normal to spend time abroad and people are not just moving once, they want to explore 10 different countries over the course of their career.” Founders who try to run one message across both buyer types end up with positioning that fully convinces neither.
Work The Category Analyst Before You Need The Category Term
GrowthSpace didn’t wait for an analyst to discover them – Omar was in active dialogue with Josh Bersin’s firm well before any category term existed. The analyst firm initially had no clean definition for what GrowthSpace was doing: “it was hard for them to define really what we are and then they came up with this new category and they said okay there is a new generation of companies that provide this type of services to companies and growspace is one of these companies who fit in.” That conversation produced the term “skill mastery platform,” which GrowthSpace then used as its category anchor in sales and marketing. The practical GTM move was treating the analyst relationship as a co-creation process, not a coverage request. Founders who approach analysts only after they have a polished category narrative are leaving one of their most powerful category-definition levers on the table.
Turn Implementation Speed Into Your Competitive Advantage
HR buyers expect nightmare rollouts because past vendors promised ease and delivered “an eight month implementation process.” Matt’s team proved speed creates differentiation: one customer called it “the easiest software that I’ve ever rolled out my entire career.” The real proof is end-user velocity. Employees go from opening “that email” to “making their first transaction” in “as little as ten minutes.” When buyers hear “this is a really seamless easy thing to roll out, red flags go off” because they’ve been burned before. Delivering actual speed turns skeptics into advocates and becomes the story customers tell prospects. — Matt Pierce
Sell To The Person Who Owns The Pain, Not The Person With The Title.
Achu built Kula’s ICP around a simple mechanic: who actually feels the problem, segmented by company size. For organizations between one and fifty employees, the answer was unambiguous — “the founders are the decision makers and they are the core pain owners so we generally sell to them.” For companies above fifty, the target shifted to the head of recruiting or the first sourcing hire, the practitioners directly accountable for building top-of-funnel pipeline. The ICP wasn’t defined by industry or geography — Kula was “function agnostic, region agnostic” — it was defined entirely by who sat closest to the pain. Title-based targeting sends you to the person who should care. Pain-based targeting sends you to the person who already does.