# Doug May

> Doug May is a Boston-based enterprise software operator, founder and managing director of Value Sherpas, and coauthor of the forthcoming book Bridging the Value Gap. Across Splunk, Databricks, Datadog and Harness, he built go-to-market systems intended to make technical value measurable, sales execution repeatable and growth less dependent on individual heroics.

- **Role:** Founder and Managing Director at Value Sherpas
- **Organizations:** Value Sherpas, Harness, Datadog, Databricks, Splunk, Bit9, Endeca, Mirror Image Internet, WebLine Communications, BBN Planet, IBM, Forbes Business Development Council
- **Education:** BS in Business Administration, University of Rhode Island, Degree unspecified, summa cum laude, Babson F.W. Olin Graduate School of Business
- **Known for:** Built and led go-to-market functions across Splunk, Databricks, Datadog and Harness during major growth periods., At Harness, reports that his teams cut account-executive ramp time by 50%, increased productivity by 43% and improved win rates fivefold through value acceleration., At Databricks, a published case study reported 80% sales adoption of its value-selling platform and win-rate improvement from 8% to 55% when reps used the business value assessment.

## Career timeline

- **Early career** — Worked in sales and sales management at IBM, BBN Planet, WebLine Communications and Mirror Image Internet.
- **Before 2011** — Served as sales director at Endeca and later held a senior sales role at Bit9, where he says he received his first CRO appointment.
- **2010s** — Joined Splunk and built a value acceleration practice that expanded from new-logo sales into expansion, renewals and product conversations.
- **2019** — Joined Databricks around its $100 million revenue stage and led Global Value Acceleration, adapting value selling to a consumption-based business.
- **2020s** — Became Chief of Staff to the CRO at Datadog, working across go-to-market execution and value.
- **2024** — Joined Harness as Senior Vice President of Productivity, overseeing functions including revenue operations, field enablement and value advisory.
- **2026** — Founded Value Sherpas, a Boston-based go-to-market advisory firm, and announced the forthcoming book Bridging the Value Gap with Wendy Wise.

## Achievements

- Built and led go-to-market functions across Splunk, Databricks, Datadog and Harness during major growth periods.
- At Harness, reports that his teams cut account-executive ramp time by 50%, increased productivity by 43% and improved win rates fivefold through value acceleration.
- At Databricks, a published case study reported 80% sales adoption of its value-selling platform and win-rate improvement from 8% to 55% when reps used the business value assessment.
- At Splunk, developed value-selling tools and practices that expanded into new-logo, expansion and renewal motions as the company grew from roughly $200 million to more than $2 billion in revenue.
- Coauthored a 2026 Harvard Business Review article on the B2B value gap with Wendy Wise.
- Writes as a member of the Forbes Business Development Council.

## Latest updates

- **2026-09** — Published a Forbes Council essay comparing revenue execution to the coordinated system behind a Formula 1 driver.
- **2026-08** — Coauthored the Harvard Business Review article Do Your B2B Customers See the Value You Deliver? with Wendy Wise.
- **2026-08** — Was identified publicly as founder and managing director of Value Sherpas after leaving Harness.
- **2026-05** — Published a Forbes Council essay arguing that sales enablement should measure demonstrated readiness rather than course completion.

## Links

- Website: https://valuesherpas.com/
- LinkedIn: https://www.linkedin.com/in/dougmay

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Profile page: https://yespress.io/doug-may
Published by YesPress — https://yespress.io
Last updated: 2026-09-27