How WorkBoard Grew Revenue 3x a Year by Selling Strategic Alignment

When Nathan Latka interviewed WorkBoard CEO Deidre Paknad in September 2018, she gave him the inputs rather than a revenue total: about 50 enterprise customers, an average contract value of about $125,000 a year, and, in her words, “we’re growing revenue three three and a half x a year.” Nathan did the multiplication on air: 50 customers at $125K “would put you at about $520,000 a month right now on revenue. Is that about accurate?” Her answer was “In the neighborhood. Yes.” That works out to roughly $6.25M a year, but it is his arithmetic, not a figure she stated, and we have found no dollar revenue figure WorkBoard has ever published. What makes the snapshot 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. Nathan’s on-air introduction credited her with “decades of experience leading enterprise and startup teams,” two Smithsonian recognitions for innovation and 16 patents. The formative chapter was PSS Systems, where she arrived as turnaround CEO in 2003. “The company raised $60,000,000 and had nothing to go to market with,” she said; it was pre-revenue. She led it for seven years, through two recessions, to an exit with “no down round, no recap,” and when Nathan asked whether everyone got their money back, she said yes. The buyer was IBM. Inside IBM she “grew the same business a whole lot more, like, 10 x more,” and in running it she “encountered this problem we solved in deep pain.”

That problem is the origin of WorkBoard, which she described as “a software company that helps other organizations align, measure and achieve their strategic priorities more quickly, more effectively.” She said she “started the company from inside IBM” and that it had launched “about four years ago”; WorkBoard’s leadership page dates the founding to 2013, with Paknad and Daryoush Paknad, its CTO, as co-founders. OKR software, in the category shorthand, though when Nathan guessed she was selling to HR managers she corrected him: “Actually not to HR managers.” WorkBoard sells to the head of the business, inside growth companies and inside huge enterprises “like a Microsoft or IBM,” because that is the person who owns the strategic priorities.

Two deliberate years of zero revenue

The seed came from “my investors in the last company,” the PSS backers she went back to with the idea, and WorkBoard’s December 2017 release puts it at $2.75 million. Paknad credits the round with buying time: “It gave us the time to get product right. And not rush the let’s add sales people. Right? And then find out we don’t have the product right.” Nathan finished the thought (“Or the funnel or the metrics or the SDR to account executive ratios”) and she agreed: “That’s right.” Revenue started in 2016.

The Series A closed, she said, in October 2017. WorkBoard announced it on December 13, 2017 as $9.3 million from Floodgate and Microsoft Ventures plus existing investors, bringing total funding to $12.1 million, which squares with her “we raised about 12,000,000.” She described spending it the way a turnaround CEO would: “building out the management team, deepening the sales team, and so on. So we’re adding, if you will, the capacity to grow at a faster rate now.” Her rule for the money: “Don’t spend it because you have it.”

$50K in July, $200K by September

By the September 2018 interview WorkBoard had about 50 enterprise customers: Sony, Samsung, Microsoft and Deutsche Telekom among the large ones, plus growth companies of a couple hundred people such as TrendKite. Asked how an account grows in its first year, Paknad gave an example from that quarter.

Here’s a typical one from this quarter. 50K first deal in July, 200K add in September.

Deidre Paknad, CEO, WorkBoard, on an account from the third quarter of 2018

So the $125K average contract value is not the landing price. In her words it is “sort of where we end up at the end of that first year,” after expansion, and it leaves out services. Expansion runs on seats: start with one part of a business unit, then add the next. Nathan computed 400% expansion on that one account and guessed net revenue retention might be “over 250 or 300%”; her answer was lower: “It probably comes out somewhere like one forty.” WorkBoard had no logo churn, she said, but it did lose revenue when customers laid people off or when the sponsoring GM lost his job, so the company tries to land a second leader in an account’s first quarter and a third in its second.

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, the substantive alignment and capturing that in the tool. … So we bring in a team of coaches that in a week or two coach teams to real alignment on real results, not tasks and activities, right, and to do lists, but on outcomes.”

Paknad described a “peak of euphoria” for that first leader on day 21, when “that leader got value beyond their expectation.” Customers pay for the coaching as an onboarding fee, and some buy it as an annualized managed service. Nathan suggested the upfront fee “probably recovers most of your CAC”; she said, “It does.” He then argued that payback was close to instant because the fee is paid upfront, and she agreed: “That’s right. Because my ACV number didn’t include my services number. … And they’re paying the service upfront and the software, annual software upfront as well.”

On overall efficiency she gave ratios rather than a dollar CAC. For most of 2017, “for every buck we were spending in sales and marketing, we were generating almost 5 in revenue.” At the time of the interview: “Right now, I’m still at 1 to about $2.50… $1 to $2.50 in revenue. … I’m trying to bring that down. I’m trying to spend more on sales and marketing.” She was not trying to hold the 2017 ratio; the target, she said, was to “spend a buck and earn two.”

WorkBoard’s revenue after the tape

What WorkBoard has published since, in dated releases, is growth rates and funding rounds, not revenue totals:

Two things in that record check against the tape. Her “three three and a half x a year” in September 2018 is consistent with the 3.5x ARR growth she later reported for the full year. And the next raise came earlier than the timetable she gave Nathan: she said she probably would not “even start the process until next April or May,” and the Series B was announced on March 20, 2019. Adding up the five announced rounds (the $2.75M seed, $9.3M Series A, $23M Series B, $30M Series C and $75M Series D) gives about $140 million raised; the company said it had raised $65 million before the Series D.

A note on our own numbers. An earlier version of this post put WorkBoard’s 2018 revenue at $6.2M. That figure was Nathan’s 50 × $125K multiplication, not something Paknad said, and it has been removed. The revenue figures on WorkBoard’s GetLatka profile are not company disclosures either: the 2023 and 2024 figures, including about $88.9M for October 2024, are GetLatka estimates, and the 2019 and 2020 rows have no recorded source. You can read the interview page with the full transcript, or watch the full 2018 interview.

Fearless, on the way out

Nathan closed with his usual question: what does she wish her 20-year-old self knew? Paknad flipped it: “In your fifties, you need to go back and say, what does my 20[-year-old] self need to tell me today? Right? And what the 20[-year-old] calls me up and says is, go fearless, man. Go fearless.” Nathan added, “You have more to protect now,” and she agreed: “You do.”