Topline · 13 Aug 2026 · From the week of 10 August
SPOTLIGHT: He Said No to Bad-Fit Customers. Growth Got Better. | Snehal Nimje, CEO & Co-Founder @ Outdoo
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Sam Jacobs hosts Topline Spotlight with Snehal Nimje, co-founder and CEO of Outdoo, an AI roleplay and coaching tool for go-to-market teams that focuses on compliance-heavy sectors. Snehal says Outdoo was close to $1M ARR and growing 20% month on month, selling to mid-market and enterprise buyers. The episode covers how selling to everyone led to chaotic product work and falling usage, how the team narrowed focus to insurance and finance, and what changed in pipeline over the following months. He argues that enterprise readiness starts with architecture and compliance, that founders should test whether customers truly need the product, and that defensibility in AI comes from owning the full workflow rather than the model.
For founders
- Enterprise buyers in regulated sectors screen on SOC 2, HIPAA, data encryption and whether the vendor runs its own LLMs before they will run a proof of concept, so build architecture and compliance from day one if you plan to sell up-market.
- Chasing every inbound lead made Outdoo's product chaotic, and usage dropped about two months after onboarding, so narrowing the ideal customer profile was treated as a fix for both growth and retention.
- Ask your best customers how big a problem you solve and whether they could do without the product, because the answers identified the sectors where Outdoo was essential.
- Spend a few hours regularly asking why something is working or not working, since Snehal said leads alone did not turn into traction until the team targeted customers who found the product essential.
- Defensibility in AI, as Snehal described it for Outdoo, comes from owning the whole customer workflow across LMS, call tracking and CRM rather than from the underlying model.
For revenue leaders
- Outdoo's customers in insurance hire agents every quarter and must clear state-specific certification before selling, which made fast ramp a compelling buying reason.
- Customers who found Outdoo essential started recommending three or four more customers, which prompted the decision to focus on one sector; Snehal said these compounding referrals help move POCs forward faster.
- Narrowing focus meant removing and repositioning a lot of content, and the pipeline dipped for about a quarter while the sales and marketing teams adjusted.
- Outdoo held town halls twice a month during the focus shift to explain the strategy and set expectations that a dip could last a quarter at most.
- Outdoo went from one meeting a week to five or six a week over roughly six months, after shifting outreach from VP Sales to L&D folks such as instructional designers who then pitched internally.
What was said 18, most useful first
Enterprise buyers in regulated sectors screen vendors on SOC 2, HIPAA, encryption and LLM hosting before they will run a proof of concept. Listen
Snehal said Outdoo's customers in legal, finance and insurance make these their first filter criteria, including whether data is encrypted and whether the vendor runs its own LLMs or uses open or third-party ones. Without these, he said, buyers do not consider a vendor even for a POC, and since POCs are needed to convert enterprise deals, this gate applies at the start of the sales cycle.
“And without these points, I mean, they don't even consider you, right? Even for the POC.”
Listen to the episode Strategy & market Link to this Report a problem
Customers who found Outdoo essential recommended three or four more customers, which led the team to focus on one sector for compounding referrals. Listen
Snehal said the team worked with customers who found the product essential, and they started recommending three or four more customers. That is when the team decided to focus on one sector, because customers recommending customers creates a compounding effect. He described this as a bridge that moves POCs faster and brings enterprise companies into the consideration stage.
“they started recommending three or four more customers.”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Outdoo shifted its outreach from VP Sales to L&D folks such as instructional designers, who then pitched internally to L&D heads. Listen
Snehal said the team had been focused on VP Sales and changed its targeting to instructional designers and L&D staff. Those contacts pitched the product internally to their L&D heads, enablement heads and similar leaders, which is how the team booked meetings during the focus shift.
“now we started focusing on the LND folks, right? Instructional designers”
Listen to the episode Pipeline & demand generation Link to this Report a problem
AI defensibility comes from solving the whole customer workflow across integrated systems, not from the AI model or a single agent. Listen
Snehal said product managers joined some sales calls and he came to suspect they were trying to copy the product and build an agent themselves. He said the real problem is the full workflow, in which roleplay feedback feeds an LMS, real calls are tracked and pushed to a CRM, and feedback returns to the rep. He said this integration becomes part of the product as models evolve.
“the problem is to solve the entire workflow, which has multiple things.”
Building and maintaining an in-house AI workflow would consume far more resources and become outdated in about six months. Listen
Snehal said organisations that try to keep updating models, workflows and MCPs themselves may spend three to five times more resources. He said a proof of concept or MVP might work for two or three months but then become outdated. He said customers who tried building this way later came back looking for a solution to the problem.
“you're spending your your spending 3x or 5x more resources, right? And you will be outdated in six months or so.”
Build the architecture and compliance certifications from day one if you intend to sell to enterprise. Listen
Snehal advised any startup going after enterprise to build its architecture and pursue compliance from the start. Sam Jacobs agreed, framing a move from SMB to enterprise as a strategic shift involving data architecture, privacy, compliance and security, not just getting a meeting with a large company.
“I suggest any startup which is actually trying to go after enterprise, build your architecture, go for compliances from day one.”
Listen to the episode Strategy & market Link to this Report a problem
Outdoo's usage fell about two months after onboarding, and customers stopped responding, during the period when it was selling to every mid-market and enterprise buyer. Listen
Snehal said the team was lead hungry and would build requested features within a day, which left the product and marketing pages cluttered. The drop in usage after onboarding, including for customers who had passed POC, prompted the team to analyse why engagement was declining. They concluded they had been onboarding any company that arrived without understanding how essential the product was to it.
“what we saw post two months of onboarding after POC or even as a customer, the usage would essentially start dropping.”
Listen to the episode Retention & customer success Link to this Report a problem
Saying yes to every customer request made Outdoo's product chaotic and its marketing pages messy. Listen
Snehal said the team would try to please any customer and ship requested features quickly, and each new request led to more requests. The result was many features and settings that made the product complicated from the product side and from the marketing side, which the team saw as part of the problem before narrowing focus.
“So it became more chaotic from the product side.”
Use feedback from champions to test how essential your product is, by asking how big a problem you solve and whether customers could do without it. Listen
Snehal said Outdoo's best customers were those whose champions gave feedback on regular calls, about every two weeks. The team asked these customers how big a problem they were solving and whether they could do without the product. Those conversations revealed that finance and insurance use cases were where the product was most essential.
“is the a product really really essential can you not do without our product right”
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In insurance, agents are hired every quarter and must clear state-specific certification before they can sell, which made fast ramp a compelling use case for Outdoo. Listen
Snehal described how insurance customers hire agents quarterly and need to ramp them quickly on legal rules, which differ by state such as Ohio and California, and by product such as life or property and casualty insurance. Each agent has to clear certification before selling. He said these nuances showed that the product was essential to these buyers, leading the team to focus there.
“every agent has to, let's say, clear certification and without that they can't actually sell.”
Listen to the episode Strategy & market Link to this Report a problem
Narrowing focus required removing and repositioning a lot of content, and the pipeline dipped for a period. Listen
Snehal said the marketing team had written extensive content to acquire leads and had to remove and reposition much of it after the decision to filter customers and focus on sectors. He said sales and marketing found it hard to say no and that pipeline went down for a time. He described the dip as lasting a quarter at most.
“we had to remove a lot of content we had to reposition our things right.”
Listen to the episode Positioning & marketing Link to this Report a problem
After the focus shift, Outdoo's meeting volume rose from one meeting a week to five or six a week, with the full change taking about six months. Listen
Snehal described a three-month plan. In the first month the team pitched and talked to customers about sectors, in the second it built conviction and crafted messaging, and in the third it had a plan that aimed for meetings in the first month. Early signs rose in a roughly linear way over the next three months, reaching five to six meetings a week, and he said the whole process took about six months.
“and eventually we were at a stage where we were consistently booking like five to six meetings in a week”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Be careful selling to L&D, because it may not hold the budget mandate, so keep pushing above that level. Listen
Sam Jacobs said that L&D does not always have the mandate for budget, so the sales team still needs to push above that level in the organisation. He acknowledged the traction Outdoo had gained while raising this caution.
“Be careful about selling the L&D. That's what I'll say. Because they don't always have the mandate for the budget.”
Listen to the episode Sales process & deals Link to this Report a problem
Leads that show interest do not necessarily create traction, so test whether customers are essential or just trying out experimental AI budgets. Listen
Snehal said Outdoo received many leads that did not lead to attraction, and that buyers who were just using experimental AI budget did not commit later. He said the team needed customers who found the product essential, and that such customers may look like small numbers early on but compound over time.
“not just because they had some experimental AI budget and they wanted to try out few things and they just did not commit later on”
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Set aside a few hours regularly to ask why something is or is not working, as a way of checking early traction. Listen
Snehal suggested founders spend at least a few hours, perhaps on a Friday morning, asking why a result is working or not working. He said Outdoo had many leads that did not turn into traction, and that this review helped the team see it needed customers who really needed the product.
“try to understand and spend at least few hours, maybe the Friday morning, right? Why is something working for you if it's working and why is something not working for you if it's not working?”
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Going after everyone without a clear thesis would confuse a startup, and early numbers from a focused segment can look small but compound. Listen
Snehal said focused customer numbers could look small in the early days, but would compound, build the company's story and help build moats. He said that without a proper thesis, pursuing every customer could confuse the company. He added that focus would have saved Outdoo maybe the first six months of the year.
“Just going and going after everyone. without a proper thesis would essentially confuse you, could confuse you.”
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Outdoo was close to $1M ARR and growing 20% month on month while selling to mid-market and enterprise companies. Listen
Snehal described the company as very close to one million ARR and in a stage between pre-seed and a later round, growing 20% month on month. He said the company was targeting mid-market and enterprise buyers, where he said things move slowly but had recently started to move faster.
“we are doing 20 % month on month”
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Outdoo ran a town hall every 15 days, twice a month, during the focus shift to keep the team aligned through the pipeline dip. Listen
Snehal said the company held town halls twice a month to explain what it was doing and how it expected things to move, and to acknowledge that a dip might come. He said that once results began to appear, the team was convinced the decision was right from a long-term perspective. He also indicated that some team members left, and that the company respected everyone's choices.
“So what actually helped us like we would do you know a town hall every every 15 days, twice in a month”
Listen to the episode Leadership & culture Link to this Report a problem