Product isn't moving fast enough
Roadmaps stall, priorities shift, and the board asks why competitors are shipping AI features while you're still in pilot mode.
For CEOs, Founders & Boards
Strong engineers. Slipping roadmaps.
The gap is rarely where you'd expect.
Nobody can tell you whether it's the strategy, the architecture, or the org — and not knowing costs more than the delay itself. That's the gap where product organizations quietly stop being effective, and it doesn't close by hiring more engineers. I've held the CTO and CPO seat, and I'm still hands-on in the architecture and the cloud bill. I can tell you which it actually is, then stay and fix it with the team you already have.
30+ years
Leading product & engineering — startups, growth-stage, Fortune 500. Still hands-on.
200 → 2,400
Organization rapidly scaled in 4 years at Virtustream, through 94% YoY growth past $500M
$5.4B+
Acquisition value of companies where Keith led product & engineering — Dell/EMC, LexisNexis, Greenway, Aptean, PaySys
CTO + CPO
Both seats held simultaneously — market strategy → build → production operations
Product & engineering leadership across Dell Technologies · SiriusXM · Cox Communications · LexisNexis Risk · Fiserv · Corpay · First Data · ChartSpan · Crypton Mobile · Aptean
The difference
One leader across the whole chain
A fractional CTO who starts at the architecture diagram can't tell you whether the market wants the thing. A fractional CPO who stops at the roadmap hands engineering a wish list. I've run both seats, and the value is in owning every link between them.
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01
Market need
Where the real pain is, who feels it, and what they already pay to make it go away.
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02
Addressable market
TAM and serviceable segments sized honestly, so investment goes where revenue actually exists.
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03
Product-market fit
Evidence over conviction — discovery, experiments, and the pricing and packaging that follow.
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04
Use-case UX
The workflow a real user completes on a real day, defined before anyone writes a ticket.
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05
Requirements
Market intent pushed down into specs engineers can build from without guessing at the why.
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06
Agile delivery
Operating rhythms, sprint discipline, and delivery accountability that survive a bad quarter.
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07
Deployment
CI/CD, release engineering, and security and compliance gates that don't stall the roadmap.
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08
Operations & resilience
SLOs, observability, incident practice, and cloud spend that behaves — shipping is the start, not the finish.
Strategy and engineering don't connect
Two capable teams, one broken handoff. Cloud costs climb, releases slip, and nobody owns the line from market opportunity to what actually ships.
You can't hire a full-time exec yet
You need a seasoned CTO or CPO now — someone who can lead the transformation, mentor your leaders, and leave the organization stronger than they found it.
Hands-on & current
I read the architecture, the code, and the cloud bill
Executive title, practitioner depth. I'm building on cloud-native PaaS across AWS and Azure today — not describing what my teams did five years ago. That depth is what makes the business judgment credible, and the business judgment is what keeps the technology pointed at revenue.
Technical depth that's current
- AWS & Azure cloud-native PaaS — serverless, containers, managed data and AI services, event-driven architecture
- AI/ML in production — copilots and intelligent features that ship, with governance a board can sign off on
- Reliability engineering — SLOs, Datadog observability, incident practice, high-volume and cluster computing
- FinOps & Well-ArchitectedSix pillarsOperational Excellence · Security · Reliability · Performance Efficiency · Cost Optimization · Sustainability review — architecture and spend held to the same bar
- Regulated builds — HIPAA/HITRUST, SOC 2 Type 2 and PCI DSS audit readiness, secure SDLC, enterprise architecture
- Roots in the deep end — .NET, C#, Python, Java, C++; network protocol and device driver development; a US patent in high-volume transaction and image processing
Business dynamics behind every decision
- Offering design — shaping a product to fit a market, then pricing and packaging it to win
- Growth strategy — redirecting technology investment toward growth: new revenue, more from the customers you already have, new markets, and cost taken out where it won't slow you down
- Organic and inorganic paths — build, buy, or partner, argued with numbers rather than preference
- M&A and diligence — technical due diligence, integration planning, and the investor-ready technology narrative
- P&L discipline — 250% revenue growth alongside $2M+ in cost reduction at LexisNexis Risk; a $120M portfolio governed for a top US broadband and media provider
- Board fluency — translating technical reality into the risk, cost, and timing language your board decides in
Why this pairing is rare. Plenty of fractional CTOs are strong engineers who go quiet when the conversation turns to segments, pricing, and where revenue comes from. Plenty of fractional CPOs are strong strategists whose plans don't survive contact with the architecture. Hiring one of each and hoping they meet in the middle is how the translation problem gets funded rather than fixed.
Services
Four ways to scope the work
Focused executive engagements, scoped to the outcomes your leadership team is measured on.
Product & AI Transformation
Shape an offering the market will pay for — and turn AI from experiment into product advantage.
- Market sizing, segmentation & product-market-fit evidence
- Product vision, roadmap alignment, pricing & packaging
- AI use-case prioritization, ROI modeling & governance
- AI product enablement: copilots, intelligent features & workflows
- Go-to-market support & launch readiness
Engineering, Cloud & Resilience
Build a platform that scales reliably, recovers gracefully, and costs what it should.
- AWS & Azure Well-Architected reviews & remediation
- Cloud-native migration, serverless/containers & FinOps
- DevOps, release engineering, SLOs & observability at scale
- Incident readiness, disaster recovery & technical debt paydown
- Security & compliance programs — HIPAA/HITRUST, SOC 2 Type 2, PCI DSS
Interim Executive Leadership
Embedded C-level leadership when you need it most — without the six-month search.
- Fractional or interim CTO / CPO (3–12 months)
- Org design, hiring, team scaling & global/offshore models
- Operating rhythms, metrics & delivery accountability
- Requirements discipline from market intent to sprint backlog
- Coaching for emerging product & engineering leaders
Strategic Transactions
Technical clarity for high-stakes decisions — investment, acquisition, or exit.
- Technical due diligence for fundraising & M&A
- Post-merger product & platform integration
- Build/buy/partner analysis & vendor negotiation support
- Investor-ready product & technology narrative
- Remediation plans that survive a buyer's diligence
Approach
Measurable progress in weeks, not quarters
A structured engagement model for executive teams who need clarity, velocity, and accountability — in that order.
Assess
One to two week audit of market position, product, engineering, and cloud readiness. Stakeholder interviews, architecture and spend review, and a prioritized roadmap with quick wins.
Align
Executive objectives, KPIs, and investment thesis mapped to 30/90/180-day milestones you can take straight to the board.
Execute
Hands-on leadership through your teams — writing requirements, reviewing architecture, standing up AI and cloud capability, and building delivery discipline that holds.
Transfer
Documentation, runbooks, and leader coaching so your people own the improved operating model and the gains keep compounding after I'm gone.
Track record
Outcomes, with the companies attached
Results delivered in executive product and engineering roles across three decades.
200 → 2,400
Scaling under pressure
Virtustream · Dell Technologies
Scaled product engineering from 200 to 2,400 people in four years through 94% YoY revenue growth past $500M, while modernizing offerings onto microservices, analytics, and responsive UX. Acquired by Dell/EMC for $1.3B.
250%
Revenue growth with cost down
LexisNexis Risk · ChoicePoint
Grew revenue 250% while cutting capital and operating expense by more than $2M. Re-engineered the data pipeline onto 30, 60, and 400-node clusters and shipped 100+ releases a year. ChoicePoint acquired by LexisNexis for $4.1B.
25%
Cloud spend cut, platform stabilized
ChartSpan Medical Technologies
As CTO and CPO, cut cloud platform expense 25% via serverless and containerization while paying down legacy debt, standing up a data lake with self-service BI, and holding HIPAA/HITRUST certification.
67%
Digital growth tied to revenue
Corpay
Lifted web traffic and new account submissions 67%, directly correlating to card revenue growth. Refactored critical legacy payment applications and launched the company's first integrated mobile self-service products.
$8M
Multi-tenant SaaS transformation
Fiserv
Led credit, lending, and payment risk analytics products serving 1,200+ financial institutions with a global team of 70+, and moved the portfolio onto a new $8M multi-tenant SaaS cloud offering.
$120M
Portfolio governance at scale
Pilar Technologies engagements
Rolled out an IT governance platform overseeing a $120M technology portfolio for a top US broadband and media provider — plus data analytics platforms for a Fortune 500 financial institution and a global data and analytics leader.
Fintech
Payments
Healthcare & Health IT
Data & Analytics Products
Enterprise Cloud
Media & Streaming
Logistics SaaS
Startups
Growth-stage SaaS
M&A Integration
Straight answers
What CEOs ask before they engage
The questions worth asking any fractional executive — answered plainly.
Are you hands-on, or purely advisory?
Hands-on, and current. I read the architecture, the infrastructure-as-code, and the cloud bill, and I'm building on cloud-native PaaS across AWS and Azure today. But depth is in service of the business case, not a substitute for it — the same person sizes the market, shapes the offering, and stands behind the architecture that delivers it.
When should a CEO hire a fractional CTO or CPO?
When you need senior product or engineering leadership without a full-time hire — during scale-up, AI adoption, cloud modernization, an interim leadership gap, or preparation for fundraising and M&A. It's also the right move when product and engineering disagree about what to build and nobody in the room can settle it with both market evidence and technical judgment.
Will I get a strategy deck and a bill?
No. The assessment produces a prioritized plan in one to two weeks, and I stay to execute it through your teams — writing requirements, sitting in sprint reviews, reviewing architecture, and owning delivery accountability against 30/90/180-day milestones you can report to your board.
How do you work with the engineering leaders I already have?
Through them, not around them. I've scaled product organizations and led global teams of 200+ across product, development, QA, SRE, and support. The measure of a good engagement is that your existing leaders are running the improved operating model after I leave — backed by documentation, runbooks, and direct coaching while I'm there.
What engagement formats and commitments are available?
An assessment sprint of one to two weeks; a 90-day transformation program; interim CTO or CPO engagements of three to twelve months; and retained fractional partnerships measured in days per month. Which shape fits depends on what you’re trying to accomplish and how much leadership capacity you already have — we settle that on the call.
What industries and company stages do you work with?
Startups through Fortune 500, with the deepest experience in fintech and payments, healthcare and health IT, data and analytics products, enterprise cloud, and media. I've built and operated under HIPAA, HITRUST, SOC 2 Type 2, and PCI DSS, and supported M&A diligence and post-merger integration on both sides of the table.
Keith Lynn · Atlanta, GA
About Keith
Thirty years building products and the organizations that ship them
I'm Keith Lynn. I've been a cofounder, a Fortune 500 VP, and a CTO who also carried the CPO title — and through all of it I stayed close enough to the technology to be useful in an architecture review. I partner with CEOs, founders, and boards to find where the market opportunity actually is, shape a product offering that fits it, and build the engineering organization and cloud platform that deliver it reliably.
I started out developing full-stack financial solutions, creating network protocols and device drivers, then cofounded a high-volume financial imaging company that grew rapidly and was acquired by the market leader in its space. I hold US Patent 5,602,936 for high-speed proof-of-deposit, check processing, and document storage management. Since then I've led product and engineering across enterprise cloud, data and analytics, financial services technology, commercial payments, and payment processing — including two companies acquired for $1.3B and $4.1B. Through Pilar Technologies, founded in 2003, I now do that work as a fractional executive.
B.S. Computer Science, University of Georgia
US Patent 5,602,936
Microsoft Certified — Azure Cloud
Certified ScrumMaster®
Certified Scrum Product Owner®
AWS & Azure Well-Architected
HIPAA / HITRUST
SOC 2 Type 2
PCI DSS
Technology Association of Georgia Cloud Board, 2016–2018
University of Georgia Student/Graduate Mentor
Engage
Let's find out whether I'm the right fit
Thirty minutes, no deck. Tell me what you're trying to ship and where it's stuck, and I'll tell you straight whether this is a fractional CTO/CPO problem, a different problem, or something you can solve without me.
keith.lynn@pilartech.com · linkedin.com/in/rkeithlynn · Atlanta, GA