Sep 8, 2022 · 20m · top-founders
She spent $100k on an agency for MVP, now has 11 FTE's and $1m ARR helping 55 brands teach their teams faster
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, Rising Team founder and CEO Jennifer Dulski explains how she bootstrapped a software-led team development platform, scaled it to $1 million in annual recurring revenue across 55 enterprise customers, and maintained high capital efficiency with a 145% net dollar retention rate.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 35.6% of the talking time here. How this is scored →
Nathan as informed peer 5.5 Guest teaching 2.7 Guest disagreement 1.2 Nathan pushing back 2.8
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:08 Defending the $100k prototype spend
Jennifer directly rejects Nathan's framing that spending $100k on an agency prototype was painful or wasted money, asserting the learnings were fully worth it.
Hardest push from Nathan ▶ 4:47 Pressing for specific customer size rangesNathan refuses vague answers about contract sizes and insists on pinning down whether the target sweet spot is 50, 1,000, or 10,000 employee orgs.
Biggest teaching moment ▶ 15:05 Correcting top-line revenue assumptionsJennifer corrects Nathan's extrapolation of $250k monthly revenue, explaining the skewed distribution of pilots versus enterprise contracts.
Nathan holds their own ▶ 6:56 Reverse-engineering net dollar retentionNathan demonstrates sharp SaaS financial acumen by connecting pilot penetration in divisions to their 145% net dollar expansion potential.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Product Architecture: Software-Led Facilitation vs. Traditional Coaching | 6 | 3 | 1 | 3 | Nathan clarifies whether the company is pure software or coaching, then pushes on pricing mechanics and how the tier structure prevents abuse. | |
| Market Positioning, Ideal Customer Profile, and Retention Numbers | 6 | 2 | 1 | 4 | Nathan repeatedly presses to pin down exact average contract values and target organization headcounts, linking expansion patterns to net retention. | |
| Founding Journey: Agency Prototype and Rebuilding the Core MVP | 6 | 2 | 2 | 4 | Nathan questions the pain of sinking $100k into an agency MVP and probes their 10-month runway, while Jennifer defends the learning value and preemptive funding. | |
| Sponsor Break: FounderPath Valuation Tool for SaaS Founders | 6 | 3 | 1 | 2 | Following the valuation sponsor break, Nathan discusses financing mechanics and Jennifer outlines the product vision of replacing static LMS systems with software facilitation. | |
| Enterprise Traction, Engagement Metrics, and Hitting $1M Run Rate | 6 | 4 | 2 | 4 | Nathan attempts to multiply logo count by ARPU to calculate MRR, prompting Jennifer to clarify their actual revenue pace and account distribution. | |
| The Famous Five: Leadership Insights and Reflections | 3 | 2 | 0 | 0 | Nathan runs through the standard Famous Five rapid-fire questions, concluding with Jennifer's reflections on age and career perspective. |
Statements from this episode (20)
Dulski: Rising Team is pure SaaS with no human coaches
“This is absolutely a SaaS product. In fact, there are no humans involved other than the leader of the team that uses our software.”
Dulski: Rising Team charges $99 per month for teams up to 11 people
“The pricing per team is 99 dollars a month per team, so a team is a manager plus up to 10 people.”
Dulski: Most Rising Team customers come through top-down sales
“And then most of our customers actually come in through kind of a top-down mechanism where a head of a division or the head of people for a company will want to use Rising Team to Increase engagement or scale their talent development.”
Dulski: Top-down enterprise deals can reach hundreds of thousands of dollars
“And those deals can be in the hundreds of thousands of dollars.”
Dulski: Rising Team has 145% net dollar retention
“And right now we're at 145% net dollar retention so far.”
Dulski pivoted Rising Team from 1-on-1 manager tool to team development
“Actually, the first prototype was about, was a tool that managers could use one-on-one with their employees. And what we learned is that it took too much time. People wanted less time and they wanted more team focus, especially in the pandemic era. And so we r…”
Dulski: Rising Team raised $3M seed round in February 2021
“We raised a three million dollar seed round in February of 21.”
Dulski: Rising Team retains about $1M from seed round
“We still have about a million dollars left from that round.”
Dulski: Rising Team burns approximately $100K per month
“No, we're probably more like a hundred K a month, but honestly, like a few deals and that is done.”
Dulski: Rising Team taking preempted capital for 24 months runway
“Not at all, actually, because we actually got preempted for some additional funding. So we are taking a bit more money now. It's going to get us another 24 months of runway.”
Dulski: Rising Team is raising on a SAFE with a higher cap
“And we're also, we're doing it on a safe, so it has a higher cap.”
Dulski: Rising Team has 11 full-time employees and 16 total
“We have 11 full-time people, and about 16 if you count the part-timers.”
Dulski: LMS platforms like Udemy have low usage and satisfaction
“There's, there are what are called learning management systems. These are flat content like Udemy or LinkedIn learning where you're watching videos and you're kind of solo doing this learning by yourself. It is Really low usage and pretty low satisfaction.”
Dulski: Rising Team is platformizing to let companies build kits
“The big idea and what we're working on now is platformizing the software so that anybody can create these interactive kits, and that means companies can too.”
Dulski: Existing accounts could yield up to $20M over three years
“I think over 12 months, it's like a million and a half to two million, and over three years, it's like 15 to twenty million, just from the customers we have already.”
Dulski: Rising Team converts 60% of demos to signed deals
“Right now we're converting 60% of demos to deals at some level.”