Workboard

Deidre Pachnod was a seasoned turnaround executive who had previously founded and led PSS Systems, a company that raised $60 million in 2003 during a recession. As a wartime CEO, she guided the company through two recessions and achieved a successful exit where investors got their money back. After the acquisition, IBM brought her in to run a larger division of the business, growing it approximately 10X. But during this time, she encountered a critical problem: companies lacked the capability and skill to create real alignment on strategic priorities across their organizations.

In 2014, Deidre left IBM to start Workboard with a clear mission: to help enterprises align, measure, and achieve strategic priorities more quickly and effectively. She raised a seed round of $2.75 million, which was substantial enough to give the team time to build the product right without rushing into sales. The company spent the first two years focused entirely on product development, walking up the stack methodically. First, they built something individual contributors loved—tools that gave frontline employees power and value. Then they added manager features to help connect strategic priorities to team work. Finally, they layered in executive dashboards for strategic alignment across the organization. This methodical approach meant the company hit revenue generation in 2016.

Workboard's go-to-market strategy relied heavily on word of mouth and inbound demand. By the time of this interview, approximately 25% of opportunities came from word of mouth, and about 45% of revenue came from the install base (expansion). The sales cycle was remarkably short at 60 days. The company demonstrated impressive unit economics: they were spending approximately $1 to generate $2.50 in new revenue, with Deidre aiming to optimize this to a 1:2 ratio as she scaled the sales team. A typical deal might start at $50K in the first month and expand to $200K by September—a 400% expansion within the first year.

The land-and-expand motion became Workboard's growth engine. The company pioneered an onboarding approach where a dedicated team of coaches facilitated substantive alignment and captured it in the tool, not just delivering software. This approach drove a peak of euphoria for the first leader on day 21, turning them into internal advocates. These customers then organically championed the tool to peer leaders, creating a viral expansion effect within large enterprises. The professional services component of onboarding recovered most of the customer acquisition cost upfront while simultaneously driving expansion to additional leaders. By 2017, before raising Series A, the company had such strong expansion momentum that 50% of its revenue came from existing customers expanding, and for every dollar spent on sales and marketing, it generated almost five dollars in revenue—though this ratio was driven partly by this exceptional expansion leverage rather than new customer acquisition efficiency alone.

Workboard now serves over 50 enterprise customers including Sony, Samsung, Microsoft, and Deutsche Telecom, with an average first-year ACV of $125K. The company is generating approximately $500-600K in monthly recurring revenue with 3.5X year-over-year growth. Net revenue retention sits at an impressive 140%, meaning the company expands within existing customers faster than it experiences churn. The 55-person team is based between Redwood City, India, and remote locations across the US. Deidre raised a Series A in Q4 of the previous year and planned to remain conservative with capital deployment, waiting until April or May of the following year to begin discussions about the next round. When asked about acquisition offers, she indicated she wouldn't sell at a 10X multiple because she believes the company's potential revenue trajectory over a 1-4 year horizon suggests much greater upside.