DWADennis W. Ashby
I build the operating systems that turn strong technology into predictable revenue.
xWithMe Follow along for my latest thinking on the industry, startups, product, sports — and the occasional light politics.
For more than 30 years, I’ve led the full commercial engine—Sales, Solutions Engineering, Customer Experience, Professional Services, and Platform Commercialization—across startups, growth-stage companies, and global enterprises.
My career has been built around a single question: How do you turn technical capability into scalable commercial outcomes?
I’ve held executive roles spanning enterprise software, AI, automation, integration, API management, and cloud, including global leadership at IBM, where I ran organizations responsible for more than $800M in revenue.
I’m usually brought in at an inflection point: growth has stalled despite strong technology, forecast confidence is slipping, or the team needs a repeatable system that makes revenue inspectable, influenceable, and predictable.
A native New Yorker (Go Knicks!) and a San Francisco transplant of 20+ years, I’ve never stopped loving the craft itself — during a recent career break I took to building WithMe end-to-end with AI coding agents. It’s what happens when an operator who still likes to ship code gets curious about what’s next.
Career Timeline
RunningChief Sales Officer
nFolks Data Solutions·Full-time
June 2026 – Present · San Francisco Bay Area
Leading revenue growth, GTM execution, partnerships, and enterprise commercialization across AI, data, cloud, and software platforms — aligning product, delivery, and commercial strategy to create durable growth.
RunningFounder & Builder — WithMe
xWithMe·Founder
January 2026 – Present · San Francisco Bay Area
Founded WithMe and shipped native iOS and Android apps solo, using AI coding agents (Codex and Claude Code). A deliberate immersion in AI-assisted product development — now live in the App Store and Google Play.
ShippedVP, Customer Experience, Alliances & Growth
Functionize·Full-time
April 2024 – January 2026 · San Francisco Bay Area
Owned post-sales economics: Customer Success, CSE, Support, Education, Services, Renewals, and Partners. Took NRR from 87% to 108%+, cut gross churn to <$100K/quarter, and built the company’s first single source of truth for customer health.
ShippedGlobal Vice President, Sales — Expert Labs (AI, Data & Automation)
IBM·Full-time
January 2022 – March 2024 · San Francisco Bay Area
Full P&L ownership of a ~$800M global business. Commercialized enterprise AI at scale — 146 AI customers, $110M AI services revenue, $300M+ pipeline, 30% YoY bookings growth, average deal size up ~3×.
- Shipped
Director, Sales — Expert Labs (Automation) — Americas
IBM·Full-time
March 2019 – December 2021 · San Francisco Bay Area
Ran the Americas Professional Services business — the regional precursor to the global role. Established Services as the connective layer of the post-sales experience with single-threaded ownership of customer outcomes. Promoted to Global VP on an accelerated track to scale the integrated Services + CS operating model globally.
- Shipped
Global Director, Client Services (Product Management Organization)
IBM·Full-time
November 2015 – March 2019 · San Francisco Bay Area
Joined IBM through the StrongLoop acquisition; immediately founded IBM’s global Client Services org for the automation and API platforms. Scaled from a 3-person nucleus to 40 people across the US, São Paulo, London, and Singapore. Made IBM’s 100% Club — top performance recognition reserved for the highest-performing executives.
ShippedHead of Customer Success & Services
StrongLoop (acquired by IBM)·Full-time
April 2014 – November 2015 · San Mateo, CA
Built Customer Success from zero at a Series A developer-tools company (LoopBack / commercial Node.js). Defined the role, engagement model, and metrics, then carried a core team into IBM to anchor the new Client Services function post-acquisition.
ShippedDirector, Customer Success & Services
Magnet Systems·Full-time
August 2013 – April 2014 · Palo Alto, CA
Built Customer Success and Onboarding from zero (0→1) at a Series B enterprise mobile backend platform. Balanced delivery speed with the reliability and security expectations enterprise IT brought to mobile backend infrastructure.
ShippedSr. Director, Customer Success & Services
Appcelerator (acquired by Axway)·Full-time
February 2012 – August 2013 · Mountain View, CA
Led a unified 60-person Customer Success and Services org through Appcelerator’s enterprise-growth phase. Operated three integrated Services functions — Design, Technology, and Advisory — with CS as the single front door.
ShippedDirector, Professional Services — Western Region
Ascendant Technology (acquired by Avnet)·Full-time
October 2007 – March 2012 · Oakland, CA
Led Western Region delivery for a systems integrator specializing in large-scale portal, integration, and security implementations — J2EE portals, ESBs, MQ, API gateways, and IAM — through to the acquisition by Avnet.
ShippedSr. Technical Account Manager
ILOG (acquired by IBM)·Full-time
September 2006 – October 2007 · Mountain View, CA
Managed strategic enterprise accounts for ILOG’s JRules Business Rules Management System — guiding customers through adoption and production deployment of rules-based decision automation in mission-critical applications.
ShippedRegional Practice Manager, West
Prolifics·Full-time
November 1996 – August 2006 · Western US
Led the Western Region professional services practice for a systems integrator specializing in J2EE application platforms, enterprise integration, and identity and access management. Built and grew the regional consulting organization over nearly a decade.
ShippedApplications Developer
KLD Labs, Inc. (acquired by Ensco)·Full-time
August 1994 – November 1996 · Huntington Station, NY
First professional role — building applications at a Long Island engineering firm. Where the career started.
