Enterprise sales strategy for startups often hits a wall somewhere in year one. There’s a moment most technical founders hit somewhere in year one. The product is real. The problem is real. But the enterprise buyer across the table wants proof that you can solve their version of the problem before they’ll commit a single dollar.
Most founders respond to that moment by pitching harder, which is a common mistake in enterprise sales strategy for startups. Howjer Gu, founder of Planoverse, responded by offering to work for free. He did it in a deliberate, structurally smart way that reflects a thoughtful approach to B2B enterprise sales, that became the engine behind Planoverse’s early enterprise sales relationships with some of Australia’s biggest retailers.
I talked to Howjer recently about how he made the jump from senior data analyst to product founder, how he got enterprise decision-makers to give a small unknown team their time, and what he’d do completely differently if he were starting today particularly when it comes to founder-led sales.. What came out of that conversation was one of the clearest frameworks I’ve heard for closing the trust gap in B2B enterprise sales, while keeping your leads and your integrity intact.
Before we get into the how, let me provide a bit of backstory to better understand how this enterprise sales strategy for startups took shape. Planoverse is a retail space intelligence platform that’s built for enterprise retailers. It handles planogramming, store layout optimization, and in-store navigation… It’s essentially the full stack of how a physical retail store gets planned, organized, and activated, making it a strong use case for B2B enterprise sales solutions. Howjer’s customers are the operations and merchandising teams inside large supermarket chains and specialty retailers across Australia, and the problems he’s solving sit at the intersection of data, physical space, and the customer experience inside the store. If you’re in retail, in a vertical adjacent to it, or building B2B software where the buyer is a large enterprise with a complex physical operation, this conversation is going to be directly relevant to you. This is especially useful if you’re building your own enterprise sales strategy for startups.
From Identifying Problems to Actually Solving Them
Howjer’s pre-Planoverse career reads like a who’s who of Australian data: Quantium, Deloitte, Commonwealth Bank, JCDecaux. He was good at the analyst role. But something about it kept nagging at him, a feeling many founders experience before entering B2B enterprise sales.
“As an analyst, you get to look at the data, you get to formulate strategies,” he told me. “But at the end of the day, you’re more of a supporting cast than someone who’s actually solving the problem. You’re finding potential ways to solve it, making recommendations. But the part I wanted to start exploring is, how do we actually solve it?”
That’s the line that separates a lot of technical people who become founders, especially those who go on to build strong enterprise sales strategy for startups, from those who stay in individual contributor roles. It’s about whether you find the identification of a problem satisfying, or whether you can’t rest until you’ve built the thing that fixes it.
I recognize that impulse. My own path from technical operator to building GTM systems for founders came from exactly the same frustration. When you can only point at what’s broken and write it up for someone else to act upon, it gets old fast.
What’s interesting about Howjer’s case is that his analyst background didn’t become irrelevant when he crossed into product. It became foundational to how he designs solutions. The details you pick up early are what let you design something that holds at the strategic level which becomes critical in complex B2B enterprise sales environments. You can’t build something coherent if you’ve never been in the weeds of the problem.
The Free Workshop Approach
When Planoverse was first trying to get enterprise retailers to pay attention, in what became a strong example of founder-led sales, Howjer was working with a clear understanding of what was possible with the technology, and a willingness to share that with no strings attached. He hadn’t yet built a case study, a recognizable brand, or a marketing budget. What he’d built was a structured way to create value before any contract conversation began.
The model was a half-hour monthly workshop, a simple but effective format within a broader enterprise sales strategy for startups. Here’s how it actually worked in practice:
Minutes 0-5: A live demo of the current prototype, including any updates since the last session. Actual product, shown directly.
Minutes 5-30: Open discussion. The retailer brought their problems. Howjer’s team brought their read on what the technology could do with those problems, and the conversation went back and forth from there.
The genius of the format is what it did for both sides which is often missing in traditional B2B enterprise sales approaches. The retailer got a look at what was possible, with a team that understood their business context and asked for nothing in return. Planoverse got a direct line into the problems they needed to build for, in real time, from the people who lived those problems every day.
“We basically helped them work through how they might solve problems with tech,” Howjer told me. “What technologies to use, how we might integrate. It was almost a joint solution design workshop. They’d give feedback on the current prototype. We’d think about how we could develop it to solve their other problems.”
That’s a paid consulting engagement, delivered free, in 30-minute increments. It worked because of something most vendors get wrong in B2B enterprise sales: they show up with a solution looking for a problem. Howjer showed up with a hypothesis and invited the buyer into the process of testing it.
Why 30 minutes specifically? Enterprise decision-makers run packed calendars which is why founder-led sales needs to be efficient and respectful of time. An hour with five of them simultaneously is nearly impossible to arrange, but half an hour is manageable. Five people is also the right group size… enough diversity of opinion to understand the business, and small enough that everyone gets a chance to speak.
He also brought food to every session which is a small touch, and a small detail that reinforces trust in B2B enterprise sales relationships, but one that’s worth mentioning.
An Elevated Relationship With “Rejection”
Here’s what this enterprise sales strategy for startups asks of you that most playbooks don’t: a completely different relationship with rejection.
Some of Planoverse’s early workshop stakeholders told Howjer the product wasn’t right for them. His response was to treat that as a product development signal rather than a closed door.
“You just need to treat it as a not yet,” he said. “Keep working on it.”
That’s only possible if you’re actually trying to solve the problem rather than just close the deal. When the motivation is right, a “not yet” gives you something useful. It tells you what’s still missing.
The workshops also had a practical effect on the contract conversation when it eventually came. By the time Planoverse sat down to negotiate, the retailer had already seen the product in action, given feedback that shaped its direction, and in some cases had Planoverse help them solve problems using the software before any formal agreement existed.
“We actually helped them for free using our software whenever they had some problems with theirs,” Howjer told me. “That really helped prove out the product before it was even live. It was already bringing some backup support value.”
By the time the buyer evaluated whether to sign, the risk felt much lower which is ultimately the goal of any enterprise sales strategy for startups. They’d already seen it work.
The ROI Conversation Most Vendors Get Wrong
Planoverse has delivered significant ROI for its retail clients. Howjer was careful about specifics, but the way he talks about measuring ROI is worth spending time on, because it’s a better framework than what most B2B enterprise sales teams use.
His position: in software, ROI is hard to measure. Most vendors do their best estimates and publicize numbers that make them look good. Howjer prefers a different approach.
“My belief is that ROI in software is very difficult to measure,” he said. “What’s more important is the agreement between the customer and the vendor. You have to come to a measure that both parties are happy with.”
That means getting aligned on the specific metric before you try to move it. Are you improving margins? Reducing labor costs? Growing basket size? Increasing customer engagement? Each of those is a different success definition, and they need to be treated as distinct.
The Planoverse approach is to decide together, early, then measure against that specific target. And when new information comes in mid-implementation, they’re willing to change the metric.
“We take a very iterative approach,” Howjer said. “We try to share that culture with our customers. We can move fast. Don’t be afraid to pivot and change up what we’re aiming for as we get more information.”
For founders running founder-led sales into enterprise accounts, this is a template you can replicate. Define ROI together upfront, against a metric you’ve both agreed reflects real business value, and build toward that specific thing.
The GTM Motion That Got You Here Won’t Get You There
Planoverse is now a team of 10, with real case studies, a rebrand in progress, and expansion across APAC in its sights. Howjer is clear-eyed about the fact that the motion that built the business can’t be the same one that scales it.
“Starting a business and going to market when you’ve just built the product is a very different thing to scaling the product,” he told me. “When we started, the workshop model was really good. Now it would be very different.”
The shift has two dimensions.
First, the product focus is changing. Early Planoverse led with tangible, internal-facing features: planogram automation, labor efficiency, operational speed. The next phase is more customer-facing. The Planoverse kiosk, for example, is an in-store device that helps shoppers navigate the retail floor, essentially Google Maps for a single store. That’s a completely different value proposition to communicate, and it requires a different kind of market visibility.
Second, the brand posture is changing. “When you’re first starting, you have to be very humble,” Howjer said. “But now we want to go out there with a bit more confidence. We have a product. We’ve already solved problems for retailers with proven case studies. We’re a full-fledged business now, and we know what we’re doing.”
That’s a real transition point. A lot of founders stay in startup-humility mode long past the point where it’s serving them. There’s a version of “we’re figuring it out together” that builds trust with early customers, and then there’s a version that signals to later-stage buyers that you’re still too early for their scale. The ability to read which mode you’re in, and adjust your positioning accordingly, is one of the underrated skills in B2B GTM.
What Howjer Would Do Differently
I asked Howjer what he’d change if he were starting Planoverse today. Three things came up immediately.
Move faster. He’d give himself a bigger risk appetite earlier. Some of the caution in year one came from founder self-doubt, the endless internal loop of “this might not work.” He’d manage that loop better now.
Bring in the team sooner. The perfectionist instinct kept Planoverse lean longer than was probably optimal. He’d hire earlier and delegate harder.
Do more outbound, sooner. “I would have spent more time reaching out, doing even more outbound,” he said. “It’s a volume game. And unless you’ve committed to a contract and failed to implement it well, reaching out doesn’t burn the bridge. If anything, it helps cultivate trust.”
That last point is something a lot of technically-oriented founders get backwards especially when they’re learning how to get enterprise clients for the first time. They treat outreach as an imposition. Howjer’s experience suggests that respectful, persistent outreach in a small TAM actually builds credibility over time, even when the first answer is no.
The Free Offer That Opens the Enterprise Door
The framework underneath Planoverse’s early enterprise sales strategy for startups is something every B2B founder should pressure-test against their own situation.
If you’re thinking about how to get enterprise clients, this framework is a useful starting point.
The real question to answer here are these:
- What free offer can I make that does real work,
- Requires real commitment from the buyer, and
- Lets them experience the value of what I’m building before any money changes hands?
For Planoverse, that was the workshop: a structured, half-hour, monthly session combining a live demo with a genuine co-design conversation. Low commitment for the buyer, and high value in both directions.
Your version will look different. But the logic holds across almost any enterprise B2B context. Make the value real before the contract is signed. Design it so that saying yes to the free offer is a small step, and saying yes to the paid engagement feels like the obvious next move.
That’s closing the trust gap with precision.
Howjer Gu is the founder of Planoverse, a retail space intelligence platform helping retailers plan, optimize, and activate their physical store environments. If you’re in the enterprise retail space or building technology that integrates with in-store infrastructure (computer vision, digital shelf labels, in-store media), reach out to Howjer directly at planoverse.com.au/contact-us.
If this piece made you think differently about how you’re opening enterprise conversations, I’d love to talk. A free strategy call is a good place to start: Book yours here.
P.S. The moment that stuck with me from my conversation with Howjer was this: he said the best salespeople aren’t the loudest ones. They’re the ones who sell in a way that fits their personality. A quieter founder is at an advantage in enterprise sales if they build a process that plays to their strengths. The workshop model is exactly that kind of process. It asks you to be truly curious about the buyer’s problem, and that’s a skill that transfers.
