How Workboard Grew to $6M in Revenue Using Strategic Alignment
Before Workboard, Deidre Paknad spent seven years turning around a company that raised $60M and shipped nothing. The second company grew to $6M revenue on a very different rule: never sell the tool before you've sold the alignment.
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When Nathan Latka interviewed Workboard CEO Deidre Paknad in September 2018, the company was doing roughly $500K–$600K a month in revenue — a run rate just over $6M — and tripling year over year. Those numbers are good. What makes them interesting is the company Paknad ran before this one, and the rule she carried out of it.
The $60M lesson she didn’t pay for twice
Paknad is not a first-time founder who lucked into enterprise sales. By the time she started Workboard she had, in Nathan’s on-air summary, “decades of experience leading enterprise and startup teams,” two innovation recognitions from the Smithsonian Institution, and 16 patents. The formative chapter was PSS Systems: a company that raised about $60M and, a couple of years in, had shipped nothing — pre-revenue, as she put it, nada. Paknad came in as the turnaround CEO, ran it for seven years, and sold it to IBM — getting the investors their money back. Then she spent a stretch inside IBM watching very large organizations struggle to point thousands of people at the same goals.
That is the origin of Workboard, which she launched in 2014 after leaving IBM: “a software company that helps other organizations align, measure and achieve their strategic priorities more quickly and more effectively.” OKR software, in the category shorthand — though Paknad was emphatic with Nathan about who the buyer is not: “actually not HR managers.” Workboard sells to the line — the executives running growth companies and huge enterprises “like a Microsoft or IBM” who own the strategic priorities themselves.
Two deliberate years of zero revenue
The move most funded founders can’t stomach: Workboard raised its seed in 2014 and stayed pre-revenue for roughly two years — on purpose — before adding a single salesperson.
Workboard raised a seed round of about $2.75M in 2014 and then did exactly that. Paknad credits her seed investor for it — “he gave us the time to get product right, and not rush the let’s-add-salespeople — and then find out we don’t have the product right. Or the funnel, or the metrics, or the SDR-to-account-executive ratios.” Revenue started in 2016. The Series A — $9.3M, per the GetLatka dataset — closed in the fourth quarter of 2017, and she described spending it exactly the way a turnaround CEO would: “building out the management team, deepening the sales team… adding the capacity to grow at a faster rate.”
$50K in July, $200K by September
By the September 2018 interview Workboard had about 50 enterprise customers — names like Sony, Samsung, Microsoft and Deutsche Telekom came up on the tape — and the shape of a deal was remarkably consistent. Asked about first-year economics, Paknad gave the pattern.
$50K first deal in July, $200K add in September.
Deidre Paknad, CEO, Workboard — on a typical account’s first year
The $125K average first-year ACV she quotes isn’t the landing price — it’s where an account ends its first year after in-year expansion. Net revenue retention worked out “around 140%.”
The engine behind that expansion is the part worth stealing. Workboard’s onboarding is not a tool walkthrough:
“They buy Workboard because they want higher alignment on the strategic priorities, they want faster results. Our onboarding process isn’t to say here’s the tool — it’s actually facilitating the alignment itself… We bring in a team of coaches, and in a week or two, coach teams to real alignment on real results — not tasks and activities and to-do lists, but outcomes.”
Paknad aims for what she calls euphoria for the sponsoring leader on day 21 — value beyond expectation, three weeks in. And customers pay for that onboarding as a services fee on top of the subscription. The arithmetic consequence, which Nathan teased out on air: customer acquisition cost was running $17K–$18K, her ACV figure excluded the services revenue, and so the paid onboarding effectively repaid CAC on day one. Overall she framed the efficiency as spending “up to a dollar to acquire two dollars and fifty cents in new revenue” — and noted the year before it had been closer to five dollars back per dollar spent, a ratio she deliberately relaxed as she added sales capacity.
What happened after the tape
The 2018 snapshot — 55 employees, $6M revenue, 3–3.5x growth — was the start of the steep part. Here is Workboard’s trajectory as captured in the GetLatka dataset:
| Year | Revenue | Team | Funding event |
|---|---|---|---|
| 2018 | $6.2M | 55 | — |
| 2019 | $18M | — | Series B, $23M |
| 2020 | $36M | — | Series C, $30M |
| 2021 | — | 358 (peak) | Series D, $75M at $725M valuation |
| 2023 | ~$71M (est.) | — | — |
| 2024 | ~$89M (est.) | 109 | — |
Total raised stands at roughly $141.6M. The headcount line tells the industry’s story as much as Workboard’s: 55 people in 2018, 358 at the 2021 peak of the enterprise-software cycle, 109 by late 2024 as the whole category reset to efficiency — the same discipline, as it happens, that Paknad preached on this tape back when money was cheap.
You can track the current numbers on Workboard’s GetLatka profile, or watch the full 2018 interview.
Fearless, on the way out
Nathan closed with his usual question — what do you wish your 20-year-old self knew? Paknad, then in her 50s with an IBM exit and a tripling company behind her, flipped it: “In your 50s you need to go back and say, what does my 20-something self need to tell me today? And what the 27-year-old calls me up and says is: go fearless, man. Go fearless. You have more to protect now.”
