Profile • Technology Executive • San Francisco
The steady hand behind two software spinouts, a sports-tech platform, and a firm that has been turning business vision into digital reality since George W. Bush was president.
The Story
In 1981, David Overmyer sat down at a local CPA firm with a fresh degree from California State University, Sacramento, and started auditing. That's where the headline is supposed to end - another accountant in a long line of accountants. Forty-five years later, he is CEO of a San Francisco engineering firm that produced two software companies that changed their respective industries.
Raw Engineering - the firm Overmyer runs - was already 11 years old when he came aboard in 2018. Founders Nishant Patel and Neha Sampat had built it into a digital product shop trusted by NBA franchises, Fortune 500 companies, and cloud-native startups. What Overmyer brought was the financial discipline of someone who had spent a decade at CBS Interactive, followed by CFO stints at Thismoment and Bunchball - two of the era's more interesting social and gamification platforms.
He had already been operating in the Surfboard Ventures orbit since 2017, serving as CFO of Contentstack - the headless CMS product Raw Engineering built and then spun out into its own venture-funded company. The trajectory of that relationship says everything about how Overmyer operates: begin with a "fractional" arrangement, demonstrate the value, and stay for seven years.
"From a boot-strapped services company 10 years ago, to building a high growth, market leading digital experience company."- David Overmyer, on Contentstack's journey
Contentstack's founder Neha Sampat called the arrangement "one of the most pivotal partnerships" of her career. Investor Cindy Padnos noted that Overmyer helped guide the company "toward the SaaS-style metrics and priorities that enabled Contentstack's rapid acceleration." That's the quiet work: the person in the room who turns revenue lines into a narrative investors can follow.
The Company
The 49 Geary Street address in San Francisco has housed some unusual ambitions. Raw Engineering - 98 employees, $7M annual revenue, AWS partner since 2007 - is the kind of firm that most people have never heard of but whose products they have probably used. Contentstack powers digital experiences for global enterprises. Built.io Flow, another Raw Engineering creation, was acquired by Software AG in 2018. The DfanX platform runs digital fan experiences for NBA teams including the Miami Heat and Sacramento Kings.
Raw Engineering's three primary service lanes - digital fan experience platforms, SaaS and mobile product development, and DevOps and cloud infrastructure - sound like the standard consulting menu. What makes Raw Engineering different is the track record of turning those services into actual products. Five SaaS products brought to market. Two companies spun out. An incubation model that most consulting firms spend decades aspiring to.
The client list reads like a cross-section of the American economy: American Airlines, Chase/WePay, VMware, Elastic, Schneider, IcelandAir. The sports vertical - Miami Heat, Sacramento Kings, the NBA's Atlanta Hawks - reflects the firm's deep investment in the DfanX platform, which delivers personalized content and real-time game information to fans year-round.
Spinouts & Products
Founded 2015 • Spun out 2018
Contentstack
The world's leading headless CMS, built inside Raw Engineering before being spun out into a venture-backed company. Overmyer served as its CFO for seven years, guiding the transition from services to SaaS.
Founded 2016 • Acquired 2018
Built.io Flow
An iPaaS (integration platform as a service) built by Raw Engineering. Acquired by Software AG in 2018. A template for how the firm incubates products from client work.
Platform • Ongoing
DfanX
Raw Engineering's digital fan experience platform, powering apps for NBA franchises and sports venues. Delivers real-time game info, loyalty wallet integration, and personalized fan notifications.
Career Timeline
1976-1981
Studied accounting at California State University, Sacramento. Graduated with a BS in Accounting and California CPA certification.
1981
Began career as an auditor at a local CPA firm - the starting point for a career that would eventually land him in the CEO chair of a San Francisco technology company.
1981-1995
Progressed through Senior Auditor and Controller roles, building foundational financial operations experience.
1995
Joined CNET Networks (later CBS Interactive Inc.) as Principal - his entry into the technology sector during the first internet wave.
1995-2007
SVP Finance at CBS Interactive. Led growth and development of financial and accounting operations across a 12-year tenure at one of the web's defining media brands.
2007-2012
CFO & SVP at Thismoment, Inc. - an early social brand content platform. First CFO role in the startup ecosystem.
2012-2017
CFO at Bunchball, Inc. - a gamification platform that pioneered enterprise loyalty programs. Another deep-dive into SaaS unit economics.
2017
Joined Contentstack as CFO. Began the fractional relationship with the Surfboard Ventures family of companies that would define his next chapter.
2018
Became CEO of Raw Engineering. Contentstack spun out as an independent company; Built.io acquired by Software AG.
2020
Co-led the pivot of 300+ Raw Engineering and Contentstack employees to remote work during the COVID-19 pandemic, maintaining 100% productivity throughout the transition.
2025
Retired from the Contentstack CFO role after 7 years. Continues as Board Director and advisor while maintaining the CEO position at Raw Engineering.
Key Achievements
Behind the Resume
Neha Sampat introduced Overmyer to the Contentstack orbit when he was still running Structure Financial Services. What started as a fractional arrangement - the kind of advisory relationship that usually stays advisory - became one of the longest-running executive partnerships in San Francisco startup history. Seven years as CFO. A board seat. The kind of continuity that is rare in a city where the average tenure in a C-suite role is measured in months.
On March 20, 2020, as the COVID-19 pandemic shuttered offices worldwide, Overmyer co-authored a blog post with Neha Sampat and Nishant Patel about how Surfboard Ventures had pivoted its entire workforce to remote work. The detail that stands out: 300+ employees across multiple countries. 100% productivity throughout the transition. The trick, they wrote, was that the Business Continuity Plan already existed. The pandemic didn't require a new plan - it required executing an existing one, daily crisis meetings, and virtual coffee breaks.
Raw Engineering has pledged 1% of its profits and time to charity - a quiet commitment that echoes the Salesforce model but gets considerably less press. For a firm with roots in cloud migration consulting, it's an interesting marker of how the company thinks about its role in San Francisco's ecosystem.
On the transition
The jump from CFO to CEO is not a linear step. It requires swapping a focus on financial stewardship for one on overall business direction, client relationships, and product vision. Overmyer made that jump at Raw Engineering in 2018 - a firm already 11 years old, with an established client base, two products being spun out simultaneously, and co-founders who remained actively involved as Founder and Chairperson.
What he brought to the role was the kind of credibility that finance executives carry in client conversations: an understanding of what enterprise customers care about beyond the product roadmap. For a firm whose clients include airlines, banks, and NBA teams, that context is not incidental to the work. It is the work.
"We're proud to have pivoted to completely working-from-home very quickly with Raw Engineering and Contentstack able to operate at 100 percent productivity throughout the transition."- David Overmyer, March 2020
"This 'fractional' relationship would become one of the most pivotal partnerships of my career."- Neha Sampat, Contentstack Founder, on working with David Overmyer
Clients & Sectors
Sports & Entertainment
DfanX Platform
Miami Heat, Sacramento Kings, NBA Atlanta Hawks. Digital fan experience apps with real-time game data, loyalty wallets, and personalized notifications.
Fortune 500 Enterprise
Cloud & DevOps
American Airlines, Chase/WePay, VMware, Elastic, ARM, Schneider. Cloud infrastructure, CI/CD pipelines, and digital transformation consulting.
SaaS & Startups
Product Development
Contentstack, Freeletics, 8x8, Inseego. End-to-end SaaS product development from architecture through launch, with a record of 5 products brought to market.
Fun Facts
Personality
Three recurring descriptors emerge from public mentions of Overmyer: methodical, steady, and loyal. The seven-year tenure at Contentstack. The fact that the Contentstack CEO still calls the original relationship "one of the most pivotal partnerships" of her career. The fact that when COVID hit in March 2020, Raw Engineering's Business Continuity Plan was already written.
In an industry that celebrates disruptors and pivots, Overmyer's career looks more like a compound interest chart than a rocket ship. Each role built on the one before it: auditor, controller, SVP finance, CFO at not-yet-profitable startups, then CEO of the firm that started it all. The financial discipline of a CPA, applied to the product ambitions of a software incubator.
When Contentstack's investors describe his contribution, they point to "SaaS-style metrics" and "financial stewardship." That's a specific kind of CEO - one who knows what the numbers have to look like before the product launch and after it.
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