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Jun 28, 2019 · 22m · top-founders

1434 She Saved a Pre Revenue $60m Raised Company, Then Launched Own Passing $6m in ARR for Team Alignment Tool

Deidre Paknad · 12m spoken Nathan Latka · 7m spoken
0:00 / 0:00

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In this interview, Workboard CEO and co-founder Deidre Paknad discusses how she scaled her enterprise strategic alignment platform past $6 million in ARR with a 140% net revenue retention rate. Drawing on lessons from her prior $60 million startup turnaround, Paknad shares her playbook for land-and-expand sales, high capital efficiency, and disciplined SaaS growth.

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 38.3% of the talking time here. How this is scored →

Nathan as informed peer 4.9 Guest teaching 3.0 Guest disagreement 1.7 Nathan pushing back 2.3
05100:0010:0020:000:01–2:27 · Nathan as informed peer 0/10 Promotional Announcement: How to Be a Capitalist Without Any Capital Solo intro and book advertisement by the host with prerecorded teaser clips; no guest interaction takes place.2:27–6:29 · Nathan as informed peer 5/10 Introducing Deidre Paknad and Workboard's Core Value Proposition Paknad immediately corrects Latka's assumption that WorkBoard sells to HR managers, explaining that business unit leaders hold strategic priorities. Latka quickly adapts and digs into her impressive turnaround CEO background at PSS Systems.6:29–9:34 · Nathan as informed peer 7/10 Scaling Workboard to 50 Enterprise Customers and Rapid ARR Growth Latka demonstrates sharp mental math by calculating WorkBoard's MRR (~$520k) and historical run-rate based on customer count and ACV. Paknad validates the figures and elaborates on early hyper-efficient acquisition metrics.9:34–12:57 · Nathan as informed peer 7/10 Unit Economics, Target Acquisition Ratios, and Enterprise TAM Latka presses Paknad on whether her hyper-aggressive CAC efficiency can hold, and drills into net retention and gross churn. Paknad explains why NRR lands at 140% despite rapid expansion due to enterprise restructuring and layoffs.12:57–16:27 · Nathan as informed peer 6/10 The Day-21 Euphoria Framework and Onboarding Coaching Paknad explains WorkBoard's Day 21 Euphoria framework and how paid human coaching accelerates product adoption. Latka connects the dots on how upfront services fees create instantaneous CAC payback.16:28–19:10 · Nathan as informed peer 6/10 Capital Strategy, Valuation Perspectives, and Sales Quotas When Latka presents a hypothetical 10x ARR buyout offer, Paknad dismisses multiple-based framing and emphasizes multi-year horizon evaluation. Latka probes into quota expectations and sales rep ramp periods.19:10–21:27 · Nathan as informed peer 3/10 The Famous Five and Reflections on Being Fearless Standard Famous Five wrap-up where Paknad delivers an insightful reflection on fearlessness in entrepreneurship, reframing what her 20-year-old self would advise her today.0:01–2:27 · Guest teaching 0/10 Promotional Announcement: How to Be a Capitalist Without Any Capital Solo intro and book advertisement by the host with prerecorded teaser clips; no guest interaction takes place.2:27–6:29 · Guest teaching 5/10 Introducing Deidre Paknad and Workboard's Core Value Proposition Paknad immediately corrects Latka's assumption that WorkBoard sells to HR managers, explaining that business unit leaders hold strategic priorities. Latka quickly adapts and digs into her impressive turnaround CEO background at PSS Systems.6:29–9:34 · Guest teaching 2/10 Scaling Workboard to 50 Enterprise Customers and Rapid ARR Growth Latka demonstrates sharp mental math by calculating WorkBoard's MRR (~$520k) and historical run-rate based on customer count and ACV. Paknad validates the figures and elaborates on early hyper-efficient acquisition metrics.9:34–12:57 · Guest teaching 3/10 Unit Economics, Target Acquisition Ratios, and Enterprise TAM Latka presses Paknad on whether her hyper-aggressive CAC efficiency can hold, and drills into net retention and gross churn. Paknad explains why NRR lands at 140% despite rapid expansion due to enterprise restructuring and layoffs.12:57–16:27 · Guest teaching 4/10 The Day-21 Euphoria Framework and Onboarding Coaching Paknad explains WorkBoard's Day 21 Euphoria framework and how paid human coaching accelerates product adoption. Latka connects the dots on how upfront services fees create instantaneous CAC payback.16:28–19:10 · Guest teaching 5/10 Capital Strategy, Valuation Perspectives, and Sales Quotas When Latka presents a hypothetical 10x ARR buyout offer, Paknad dismisses multiple-based framing and emphasizes multi-year horizon evaluation. Latka probes into quota expectations and sales rep ramp periods.19:10–21:27 · Guest teaching 2/10 The Famous Five and Reflections on Being Fearless Standard Famous Five wrap-up where Paknad delivers an insightful reflection on fearlessness in entrepreneurship, reframing what her 20-year-old self would advise her today.0:01–2:27 · Guest disagreement 0/10 Promotional Announcement: How to Be a Capitalist Without Any Capital Solo intro and book advertisement by the host with prerecorded teaser clips; no guest interaction takes place.2:27–6:29 · Guest disagreement 3/10 Introducing Deidre Paknad and Workboard's Core Value Proposition Paknad immediately corrects Latka's assumption that WorkBoard sells to HR managers, explaining that business unit leaders hold strategic priorities. Latka quickly adapts and digs into her impressive turnaround CEO background at PSS Systems.6:29–9:34 · Guest disagreement 1/10 Scaling Workboard to 50 Enterprise Customers and Rapid ARR Growth Latka demonstrates sharp mental math by calculating WorkBoard's MRR (~$520k) and historical run-rate based on customer count and ACV. Paknad validates the figures and elaborates on early hyper-efficient acquisition metrics.9:34–12:57 · Guest disagreement 2/10 Unit Economics, Target Acquisition Ratios, and Enterprise TAM Latka presses Paknad on whether her hyper-aggressive CAC efficiency can hold, and drills into net retention and gross churn. Paknad explains why NRR lands at 140% despite rapid expansion due to enterprise restructuring and layoffs.12:57–16:27 · Guest disagreement 1/10 The Day-21 Euphoria Framework and Onboarding Coaching Paknad explains WorkBoard's Day 21 Euphoria framework and how paid human coaching accelerates product adoption. Latka connects the dots on how upfront services fees create instantaneous CAC payback.16:28–19:10 · Guest disagreement 4/10 Capital Strategy, Valuation Perspectives, and Sales Quotas When Latka presents a hypothetical 10x ARR buyout offer, Paknad dismisses multiple-based framing and emphasizes multi-year horizon evaluation. Latka probes into quota expectations and sales rep ramp periods.19:10–21:27 · Guest disagreement 1/10 The Famous Five and Reflections on Being Fearless Standard Famous Five wrap-up where Paknad delivers an insightful reflection on fearlessness in entrepreneurship, reframing what her 20-year-old self would advise her today.0:01–2:27 · Nathan pushing back 0/10 Promotional Announcement: How to Be a Capitalist Without Any Capital Solo intro and book advertisement by the host with prerecorded teaser clips; no guest interaction takes place.2:27–6:29 · Nathan pushing back 2/10 Introducing Deidre Paknad and Workboard's Core Value Proposition Paknad immediately corrects Latka's assumption that WorkBoard sells to HR managers, explaining that business unit leaders hold strategic priorities. Latka quickly adapts and digs into her impressive turnaround CEO background at PSS Systems.6:29–9:34 · Nathan pushing back 2/10 Scaling Workboard to 50 Enterprise Customers and Rapid ARR Growth Latka demonstrates sharp mental math by calculating WorkBoard's MRR (~$520k) and historical run-rate based on customer count and ACV. Paknad validates the figures and elaborates on early hyper-efficient acquisition metrics.9:34–12:57 · Nathan pushing back 5/10 Unit Economics, Target Acquisition Ratios, and Enterprise TAM Latka presses Paknad on whether her hyper-aggressive CAC efficiency can hold, and drills into net retention and gross churn. Paknad explains why NRR lands at 140% despite rapid expansion due to enterprise restructuring and layoffs.12:57–16:27 · Nathan pushing back 2/10 The Day-21 Euphoria Framework and Onboarding Coaching Paknad explains WorkBoard's Day 21 Euphoria framework and how paid human coaching accelerates product adoption. Latka connects the dots on how upfront services fees create instantaneous CAC payback.16:28–19:10 · Nathan pushing back 4/10 Capital Strategy, Valuation Perspectives, and Sales Quotas When Latka presents a hypothetical 10x ARR buyout offer, Paknad dismisses multiple-based framing and emphasizes multi-year horizon evaluation. Latka probes into quota expectations and sales rep ramp periods.19:10–21:27 · Nathan pushing back 1/10 The Famous Five and Reflections on Being Fearless Standard Famous Five wrap-up where Paknad delivers an insightful reflection on fearlessness in entrepreneurship, reframing what her 20-year-old self would advise her today.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 95.4% · guest 4.6%0:00 · Nathan 95.4% · guest 4.6%3:00 · Nathan 19.8% · guest 80.2%3:00 · Nathan 19.8% · guest 80.2%6:00 · Nathan 23% · guest 77%6:00 · Nathan 23% · guest 77%9:00 · Nathan 26.8% · guest 73.2%9:00 · Nathan 26.8% · guest 73.2%12:00 · Nathan 18.4% · guest 81.6%12:00 · Nathan 18.4% · guest 81.6%15:00 · Nathan 36.2% · guest 63.8%15:00 · Nathan 36.2% · guest 63.8%18:00 · Nathan 29.6% · guest 70.4%18:00 · Nathan 29.6% · guest 70.4%21:00 · Nathan 78.8% · guest 21.2%21:00 · Nathan 78.8% · guest 21.2%
Sharpest disagreement ▶ 17:31 Rejecting the 10x multiple acquisition framing

Paknad flatly turns down a hypothetical 10x ARR acquisition offer, dismissing valuation multiples in favor of evaluating 1-to-4-year revenue potential.

 Hardest push from Nathan ▶ 11:30 Latka probing under the hood of net revenue retention

Latka refuses to accept high-level expansion claims at face value, pressing Paknad on exact net revenue retention percentages and underlying gross churn drivers.

 Biggest teaching moment ▶ 3:03 Paknad corrects Latka on enterprise buyer persona

Paknad immediately corrects Latka's assumption that WorkBoard is an HR tool, explaining why strategic alignment sits with business unit general managers.

 Nathan holds their own ▶ 7:40 Latka calculates exact MRR and prior year baseline

Latka demonstrates strong financial intuition by instantly calculating WorkBoard's current $520k MRR and reverse-engineering their $175k baseline from the previous year.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Promotional Announcement: How to Be a Capitalist Without Any Capital 0000 Solo intro and book advertisement by the host with prerecorded teaser clips; no guest interaction takes place.
Introducing Deidre Paknad and Workboard's Core Value Proposition 5532 Paknad immediately corrects Latka's assumption that WorkBoard sells to HR managers, explaining that business unit leaders hold strategic priorities. Latka quickly adapts and digs into her impressive turnaround CEO background at PSS Systems.
Scaling Workboard to 50 Enterprise Customers and Rapid ARR Growth 7212 Latka demonstrates sharp mental math by calculating WorkBoard's MRR (~$520k) and historical run-rate based on customer count and ACV. Paknad validates the figures and elaborates on early hyper-efficient acquisition metrics.
Unit Economics, Target Acquisition Ratios, and Enterprise TAM 7325 Latka presses Paknad on whether her hyper-aggressive CAC efficiency can hold, and drills into net retention and gross churn. Paknad explains why NRR lands at 140% despite rapid expansion due to enterprise restructuring and layoffs.
The Day-21 Euphoria Framework and Onboarding Coaching 6412 Paknad explains WorkBoard's Day 21 Euphoria framework and how paid human coaching accelerates product adoption. Latka connects the dots on how upfront services fees create instantaneous CAC payback.
Capital Strategy, Valuation Perspectives, and Sales Quotas 6544 When Latka presents a hypothetical 10x ARR buyout offer, Paknad dismisses multiple-based framing and emphasizes multi-year horizon evaluation. Latka probes into quota expectations and sales rep ramp periods.
The Famous Five and Reflections on Being Fearless 3211 Standard Famous Five wrap-up where Paknad delivers an insightful reflection on fearlessness in entrepreneurship, reframing what her 20-year-old self would advise her today.

Statements from this episode (16)

Assertion Not checkable as stated
Workboard averages $125,000 ACV across its enterprise and growth customers
“Actually, we think of, we do annual contracts. We sort of think of what their ACV per customer is, and it's about a 125 K. We've got really large enterprise, like a Sony, Samsung, Microsoft, right? Do it to telecom. And we've got a bunch of growth companies, a…”
Deidre Paknad Jun 28, 2019 ▶ 3:49
Disclosure
Workboard has raised about $12M to date
“We've raised about twelve million.”
Deidre Paknad Jun 28, 2019 ▶ 5:15
Assertion Contradicted
Paknad joined PSS Systems when it had raised $60M without a product
“I started in 2003. The company had raised sixty million bucks and had nothing to go to market with.”
Deidre Paknad Jun 28, 2019 ▶ 5:47
Assertion Not checkable as stated
PSS Systems exited to IBM without a down round or recapitalization
“Ended up with an exit that was no down round, no recap. Got to value on, on that capital.”
Deidre Paknad Jun 28, 2019 ▶ 6:08
Assertion Not checkable as stated
Workboard has 50 enterprise customers and grows revenue 3x-3.5x year-over-year
“So we have about 50 enterprise customers, which I think of at that kind of scale we just talked about, and we're growing revenue three, three and a half X a year, so we're really kind of a good role.”
Deidre Paknad Jun 28, 2019 ▶ 7:15
Assertion Not checkable as stated
Workboard is generating approximately $520,000 in monthly recurring revenue
“In the neighborhood.”
Deidre Paknad Jun 28, 2019 ▶ 7:52
Assertion Not checkable as stated
Workboard draws 50% of revenue from its existing install base
“We had 50% of our revenues coming from our install base”
Deidre Paknad Jun 28, 2019 ▶ 8:14
Assertion Not checkable as stated
Workboard generated almost $5 in revenue for every $1 spent on sales
“We even got to a point where for every buck we were spending in sales and marketing, we were generating almost five in revenue. Nathan Latka: When was that? What year? Deidre Paknad: Last year. Just before I raised, right? So for most of 2017, that was a ratio”
Deidre Paknad Jun 28, 2019 ▶ 8:29
Disclosure
Workboard targets generating $2 in revenue per $1 spent on sales
“We, we're actually not trying to hold quite that aggressive a ratio, right? So we really want to spend a buck and earn two.”
Deidre Paknad Jun 28, 2019 ▶ 9:54
Assertion Not checkable as stated
Workboard's net revenue retention rate is approximately 140%
“It probably comes out somewhere like one 40.”
Deidre Paknad Jun 28, 2019 ▶ 11:44
Assertion Not checkable as stated
Workboard claims zero logo churn despite layoff-driven revenue contraction
“So we don't have logo churn. We do have gross revenue churn and those that comes from two places. Literally layoffs are a real thing. Right. Companies like IBM, for example, which is a customer and the GM loses his job.”
Deidre Paknad Jun 28, 2019 ▶ 12:06
Assertion Not checkable as stated
WorkBoard's upfront onboarding fees recover most of its customer acquisition cost
“It does, and it drives that attach rate to leader number two, number three, and number four.”
Deidre Paknad Jun 28, 2019 ▶ 14:17
Assertion Not checkable as stated
Workboard's enterprise sales cycle is about 60 days
“Sales cycle is about 60 days, super short, right?”
Deidre Paknad Jun 28, 2019 ▶ 14:51
Disclosure
Workboard plans to delay its next fundraising process until Spring 2020
“So we probably won't raise until, even start the process until next April or May.”
Deidre Paknad Jun 28, 2019 ▶ 16:48
Disclosure
Paknad rejects the idea of selling Workboard for a $100M valuation today
“Not today.”
Deidre Paknad Jun 28, 2019 ▶ 17:31
Assertion Not checkable as stated
Paknad secured a $10M deal from her first business pitch at 24
“So I was in my first startup when I was 24. I, like, made my first business pitch to another company, and they ended up writing us a ten million dollar check.”
Deidre Paknad Jun 28, 2019 ▶ 20:14
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