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Strategic Communications Advisory For Visionary Founders
17 HR Tech Founders
Positioning & Messaging Lessons
Use the Buyer's Own Language When Positioning Your Product
Nitzan tried to create a new category that consolidated two existing product layers under a single name, and sales stalled. “We set up a new name and a campaign, and we explained that. And no one will buy. I mean, a few, but very few bought it. It was very tough for them to understand because that’s not how they used to buy.” When he reverted to the familiar category labels buyers already used, the dynamic shifted immediately. “Only when we change it to actually name the layers as they used to be, they started to say, oh, now I understand. So I invite you to the RFP about this.” The lesson Nitzan drew was direct: “Sometimes it’s better to think of how a buyer is, especially enterprise, and, you know, we are selling to those mega clients. How do they know what to buy? How can they buy solutions?”
Expose the Market Assumption Your Competitors Have Accepted
Jason built Electives’ positioning around a single flawed assumption baked into the corporate training market. “There’s this assumption that’s been kind of long in this market of if you need corporate training, well, you must go to people who call themselves corporate trainers. And that to us was this big miss in terms of who we could be learning from.” By naming that assumption and explicitly rejecting it, the existing market stopped looking like competition and started looking like a problem to solve. “We fundamentally kind of set out to not necessarily work with your, typical corporate trainer. We built a platform and a marketplace of teachers who are FBI agents and professional athletes and professors and authors and all kinds of interesting people who are amazing teachers. They just don’t wake up out of bed every morning calling themselves a corporate trainer.”
Show Buyers the Problem They Cannot See From Their Seat
Matt Pierce identified a structural empathy gap at the center of Immediate’s sales process: the HR leaders and executives making the buying decision were personally insulated from the financial reality their employees faced every day. To close that gap, Immediate built a financial stress report designed to make the problem visceral for buyers. As Matt explained, “a lot of what that report is doing is helping people open their eyes to the fact just because I may be a C-level or a head of HR who’s a little bit removed from that, feels comfortable, has some money put aside for savings, is making a good salary. Really trying to help them understand the plight of the paycheck to paycheck worker.” Specific data points anchored the conversation: “87% of our users are earning less than $50,000 a year. So when you look at it in this pay demographic, those are the people that are having a really difficult time living paycheck to paycheck and making sure that they’re taking care of their families.” Giving buyers a clear picture of a reality they had never lived made the problem harder to dismiss.
Name Your Subcategory to Avoid Being Compared to Legacy Solutions
When BrightHire decided how to position in the market, Ben talked about the risk they were trying to avoid: “We didn’t want to get bucketed with solutions that were truly pretty fundamentally different in terms of the way that they’re used and the value that they create.” The existing video interviewing category had legacy players whose products bore little resemblance to what BrightHire was building, and being compared to them would have undermined the value they were trying to communicate. Their response was to name the difference explicitly and own it: “The subcategory interview intelligence is new. We are the leader, we’ve educated the market and we can talk about that process.” Defining the subcategory gave them a way to acknowledge the broader space buyers already understood while making clear that what BrightHire did was a distinct and separate thing.
Lead With the Problem Your Buyer Wants to Eliminate
Jeremy understood that his buyers, CTOs and engineering leaders, had a specific fear around global hiring that had nothing to do with talent quality. It was operational dread. “How many CTOs or heads of engineering want to think about labor law across the world? In fact, this is why most companies, even today, try to limit how many countries they operate in.” Andela’s positioning addressed that fear directly. As Jeremy put it, “what I care about is that the companies that are working with us don’t have to think about compliance or labor law, because we’re going to deal with it for them.” The result was a value proposition framed around elimination rather than addition: “Andela enables you to think about the world as a hiring platform without having to deal with any of that complexity yourself.” When your buyer has a job they actively hate doing, making that job disappear is often a more compelling message than any feature you can lead with.
Differentiate Your Messaging by Stating Hard Truths Competitors Avoid
Michael looked at how every competitor marketed in the L&D space and saw the same pattern: vague claims, industry jargon, and a complete unwillingness to take a hard stance on anything. “If you look at everyone’s marketing in the space, there’s a lot of buzzwords that make little to no sense. No one’s really clear about what they do. You have to hop on the phone with a sales rep to figure out what the company actually does. No one’s willing to share hard truths.” His response was to build Arist’s messaging around the opposite approach. “A lot of our approach to marketing has just been being very honest, very blunt, very different from everybody else, and just willing to have hard conversations that for some reason other companies aren’t willing to have because they’re afraid that it will backfire.”
Translate Technical Positioning Into Language Your Buyer Already Speaks
Hanns made an abstract data platform immediately understandable by anchoring the positioning to a familiar reference point. “I really like to compare us to the Google Maps for skills, meaning. So Google Maps is kind of the source of truth for navigating to your grocery store or your restaurant. You don’t enter street names anymore when you use Google Maps. You enter the grocery store, the restaurant. And the same way we want to act as you define your next job role that you want to get to. And we take care of what are the exact skills that you navigate towards that job role.” The analogy also communicated the platform’s role as underlying infrastructure for other services: “the same way Google Maps provides its maps data as an API to Uber and Lyft and Uber Eats, we would deliver our skills API to all those HR services that have courses or roles or recruiting use cases.” A well-chosen analogy can communicate both function and business model in a single sentence.
Position Your Product as a Tool That Empowers Buyers to Succeed
Crosschq’s early messaging led with the problem in the bluntest possible way, and it backfired. As Mike described it, they were “coming into companies with a big bat, telling them that you’re not doing a good job of this, you’re not doing a good job of your hiring.” The team realized quickly that this approach misread the buyer: “this buyer is doing the best they can do.” The fix was a reframe, moving from a message that exposed failure to one that offered capability. In Mike’s words, “just empowering them versus coming in and telling them what they’re not doing, they’re two very different things and two very different motions and two very different ways of communicating. We kind of had to figure that out.”
Build Your Messaging Around the Emotional Outcome Your Buyer Actually Wants
Jared Pope grounded Work Shield’s brand positioning in a specific insight about what buyers actually want from the product. “At the end of the day, what we find is when someone’s been potentially harassed or discriminated against or there’s some misconduct that happens in the workforce, at the end of the day, the employee that it happens to, they just want to know that their voice is heard and that the company is actually going to take it seriously.” That insight shaped the brand directly: “When we started with our brand of Work Shield Be Heard, we really meant it. Where the employee could be heard, the employer is obviously heard through the investigation and making sure that things are done.” The message was built around that emotional outcome, not around features or process.
Tailor Your Messaging to Match the Seniority of Your Buyer
As Metaview’s buyer profile shifted from individual end users to senior leaders, Siadhal recognized that the same messaging stopped working. “We used to focus the product demos almost on the end users. But as we’ve got more traditional buyers, let’s say you’re VP of talent acquisition or your VP of recruiting, of course they don’t sort of necessarily care as much about the low level features.” What senior buyers wanted was a different conversation entirely. “They care more about what’s the broad arc, the broad trend that I can fit this company in or maybe even fit this person in and how they’re going to help me.” His response was to add a new layer to the mix rather than replace what was working: “we’ve started to change or add, I would say to the mix a bunch of broader how is AI affecting recruiting talk points.”
Mirror the Competitive Frustration Your Buyer Already Carries
Sid built WizeHire’s core message around a tension his buyers were already living: competing for talent against much larger organizations with dedicated recruiting resources. As he put it, “we’re essentially helping small businesses to get the same quality experience as the Fortune 500s that they often compete with, that have recruiting resources and have staffing dollars. That’s the David and Goliath story that we play.” The framing works because it names a real asymmetry the buyer recognizes before the conversation even starts. Sid sharpened that contrast further: “for them, it’s a game of luck and chance versus skill. Because if you think about those Fortune 500s, they have a machine that is built to process resumes, run the interview process. The conversation that we have with customers is teaching them these best practices in an easy and accessible way.” When your messaging mirrors the frustration your buyer already carries, you skip the work of convincing them the problem exists.
Connect Your Differentiator Directly to the Buyer's Biggest Objection
Andres described breaking through in a crowded market as starting with one specific discipline: “the most important thing that you can do to stand out is, first, really understand what your differentiator is and be able to verbalize that very quickly.” He pointed to what Fetcher did differently, explaining that what “95% of our competitors don’t do” was the core of the message he brought into sales conversations. He also described the buyer dynamic that made that message relevant, with skeptical prospects asking “I’ve tried before and it didn’t work. What can you tell me that’s going to work this time?” His observation was that once you explain the differentiator clearly, “you explain the human part and they get it.” He added that beyond the differentiator, sustained execution on the product experience also played a role: “you need to have, an incredibly intuitive, easy to use platform that automates a lot of the functionality around engaging, cracking, re-engaging.” Andres framed this combination as how you get your foot in the door and build from there.
Tie Your Messaging to Macro Trends Your Buyers Already Care About
Charlotte found that connecting the product story to broader workforce trends immediately changed how buyers understood what the product solved. “We kind of came up with some of this new messaging around tying the macro trends to what we’re doing and really seeing that’s really helping people to understand what we do, the problems we solve.” The team brainstormed the new message, tested it with a handful of clients, and the market responded fast. “Within a month that whole story was covered by Forbes and I was like, guys, we got to take a moment here. That was really fast. Like we came up with this, we brainstormed, we tested on a few clients and it was in Forbes within, you know, four weeks.”
Earn Thought Leadership When Buyers Cannot Search for What You Sell
When your category doesn’t fully exist yet, buyers can’t search for what they don’t know they need. Karoli Hindriks addressed this by focusing Jobbatical’s marketing energy on earning presence in high-level conversations about immigration and international hiring rather than chasing demand that wasn’t there yet. “One thing that we have done and managed to do quite uniquely is really bringing the discussion of immigration visas, 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.” That credibility compounded over time and opened doors that paid media couldn’t. “Just before we did our series A, I was asked to speak at the main TED stage in America which doesn’t happen very often at the early stage.”
Run Deep Positioning Work Before Writing a Single Message
Wingspan under-invested in positioning early because the team was heads-down building the product. “This is part of the company that we didn’t invest in as much as we should have in the early days,” Anthony said. When they finally addressed it, the work went deep: “We went through a very deep positioning and segmentation and messaging exercise of what are the competitive alternatives and where do we fit into somebody’s life and in their context.” That exercise forced clarity on the competitive landscape, including how to position against established players that buyers already trusted. As Anthony put it, the challenge was competing against tools that “are not purpose built for this specific industry or this specific use case.”
Position Against the Reality Your Buyer Lives In
Prem Kumar identified that the competitive frame most buyers assumed was wrong, and he corrected it directly in his positioning. “The problem with these high volume jobs is 80% of them weren’t getting to talk to a human anyways. And the 20% that were, were waiting a week to schedule it or two weeks to schedule it. So it’s not necessarily comparing automation and chatbots to a human.” The real comparison was automation versus silence, and that reframe made the value proposition significantly stronger. “I think if we had unlimited humans, that would be great, we could talk to everyone, but that is impossible.” When your buyer is measuring you against an ideal that doesn’t exist in practice, shifting the benchmark to the actual status quo changes the entire conversation.
Track Buyer Purchasing Criteria to Drive Positioning Decisions
Tony Jamous built a systematic framework to capture why deals were won or lost, which he called buyer purchasing criteria. “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.” He framed this as a continuous obligation for any founder or product marketing leader, not a periodic exercise. “I think that’s an iterative problem that every founder or product marketing leader needs to be obsessed with and continuously fine tune and refine that positioning in the market and have ways to track it, and have some mature data driven infrastructure that enables you to iterate fast.”