Lancaster County, PA · Fractional CTO

Senior tech leadership.
Real AI experience.

Only 48% of digital initiatives hit their business targets (Gartner, 2026). The other half don't miss on tooling — they miss on the chain that produces results: strategy that picks the right work, coaching that prepares the team to run it, execution that ships. Most consultants do one piece. We do all three, on retainer, for Lancaster County companies that have outgrown "ask the developer" but aren't ready for a $300K hire. 20+ years leading engineering and product transformation. Eight AI products live in production right now.

• 20+ years transformation & leadership • Fortune 500 background • Lancaster County local
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60-second assessment. Or book a fit call. Or talk to our AI receptionist: (717) 366-9431

Tech & AI Opportunity Score

A real diagnostic across six pillars — not a marketing form. Answer nine questions, get a multi-axis read on where the leverage actually is in your business.

01 / 09
What industry is your company in?
02 / 09
How many people are on your team?
03 / 09 · Strategy
How clear is your 12-month technology direction?
04 / 09 · Transformation
How does your business decide which technology projects to prioritize?
05 / 09 · AI Strategy
What's your current relationship with AI?
06 / 09 · Architecture
How well do your current systems work together?
07 / 09 · Process Excellence
When you make a technology change or hire a vendor, how do you measure whether it worked?
08 / 09 · Leadership
What's your biggest people challenge with technology?
09 / 09 · What would help most
What would actually help you most right now?
0
Book a Discovery Call — Free

30 minutes. We'll walk through your score, name where the real leverage is, and tell you honestly whether we're the right fit — or who is.

When you need this

A few signs it's time.

A few patterns that come up in conversations with companies thinking about a Fractional CTO. Read the list and decide what fits.

i.

Tech decisions piling up

You have engineering decisions to make — tooling, architecture, security, AI — and no one in the room with enough scars to make them well.

ii.

Vendors are confusing

Every SaaS vendor sounds the same in their pitch deck. You want a neutral voice helping you evaluate fit, contract terms, and total cost of ownership.

iii.

You're hiring engineers

Nobody on your team can interview a senior backend engineer. Job specs are vague, and the wrong hire would set you back six months.

iv.

Tech debt is slowing the business

The platform that got you to here won't get you to the next milestone. You need a triage and a roadmap, not a rebuild.

v.

Compliance pressure

HIPAA, SOC 2, PCI — your customers are starting to ask. You need someone who's done this before guiding the response.

vi.

AI is everywhere — what's real?

Half your team thinks AI is a fad, the other half wants to rebuild everything around it. You need someone who can separate signal from noise.

What's included

Six things, done well.

A Fractional CTO retainer covers the whole chain — strategy, transformation, AI, architecture, process, and leadership. Six pillars, one experienced practitioner, one retainer. The judgment that doesn't fit a project scope, applied across all of it.

i.

Strategy

  • Technology roadmap aligned to business outcomes
  • Vendor evaluation, build-vs-buy analysis, RFP support
  • Quarterly strategic reviews with leadership
  • Risk assessment — security, compliance, vendor lock-in
  • Trusted third voice when leadership is split on a technical call
ii.

Transformation

  • Operating model design — bringing business and technology into alignment
  • OKR adoption and quarterly planning cadence
  • Agile and lean adoption at the right scale (no blanket frameworks)
  • Team-level coaching for scrum masters, POs, and engineering leads — story mapping, retros, backlog refinement, sprint discipline
  • The rhythms that make change stick — not just the kickoff
  • Continuous improvement that compounds quarter over quarter
iii.

AI Strategy

  • Where AI actually pays back — and where it doesn't
  • Model and tool selection (Claude, GPT, MCP, Copilot, vendor stacks)
  • AI governance — data, security, compliance, audit trails
  • Implementation oversight so pilots don't end up shelfware
  • Concordance scoring on AI risk and deployment posture
iv.

Architecture

  • System architecture review and recommendations
  • Technical debt triage with prioritized remediation
  • Integration design — CRMs, ERPs, ticketing, AI tooling
  • Production readiness posture — observability, instrumentation, resilience
v.

Process Excellence

  • Process and rhythm at the team level — refinement that produces shippable work, planning that doesn't drift, retros that surface real action
  • Engineering hygiene and best practices — review discipline, testing standards, deployment cadence (set at policy level, not the line)
  • SDLC governance — branching strategy, release management, environment posture, incident response
  • Delivery flow and predictability — lead time, throughput, planning hygiene
  • Concordance scoring across overall health, compliance evidence, AI risk, and deployment risk — same engine we run on our own systems
vi.

Leadership

  • Designing the technical leadership org — chapters, squads, manager structure
  • Hiring rigor — job specs, interview design, performance baselining
  • Mentorship and office hours for your engineering leads
  • Structure decisions — when to promote, when to hire, how to scale managers
  • Vendor and contractor oversight when you outsource
How it works

The first 90 days.

Engagements start with a free 30-minute fit call. If we're a fit, here's what the first quarter looks like.

Days 1–30

Listen, baseline, prioritize.

Deep dive into your current state — tools, team, code, vendors, customers. Output: a written assessment with your top 5 risks and top 5 opportunities, ranked.

  • Stakeholder interviews
  • Architecture & tooling review
  • Vendor & contract audit
  • 30-day written report
Days 31–60

Plan, decide, move.

Translate the assessment into a roadmap. Make the highest-impact decisions you've been avoiding. Get the team unstuck.

  • 12-month technology roadmap
  • 2–3 vendor or build-vs-buy decisions
  • Hiring plan, if applicable
  • Tech-debt remediation queue
  • Weekly leadership sync
Days 61–90

Execute, measure, adjust.

Ship the first wave of decisions. Establish the rhythms that make ongoing engagement valuable: monthly reviews, quarterly planning, on-demand judgment calls.

  • First wave of decisions executed
  • Quarterly planning cadence in place
  • Monthly governance review
  • Engineering metrics dashboard
  • Roadmap revised against reality
Pricing

One tier. Plain pricing.

Fractional CTO

Experienced leadership on retainer.

$4,500 / month
6–10 hours per month · quarterly 90-minute on-site working session · 90-day initial commitment, then month-to-month
Roughly 22% of a full-time CTO's loaded cost. Below comparable fractional CTO retainers nationally.

Best fit

  • 10–200 person companies in PA / mid-Atlantic
  • Experienced technical perspective when you want it — driving the call, advising on it, or being the trusted voice when something's hard
  • Founder or COO who wants a thinking partner, not a contractor
  • Financial services, insurance, manufacturers, distributors, professional services, multi-location retail and grocery

Anti-fit

  • You want me writing production code as the deliverable (build work scopes separately inside the engagement)
  • You need 30+ hours/month of CTO time (at that point, hire one)
  • You haven't named an internal person to work with me
  • You need an MSP — we'll refer you
Book a Fit Call →

What we've built

9
Products & experiments live in production
6
AI integrations shipped — Claude, Grok, Retell voice, native MCP server
13
Production API integrations — payments, dev tools, market data, AI
4
Active agile, lean & product coaching certifications — ICP-ACC, SAFe Trainer, CSM, PAL

Who you'll actually work with

Hi, I'm Terry.

20+ years in enterprise tech — started in tech support, moved through hands-on engineering and agile coaching, ended up in Fortune 500 leadership across financial services, insurance, advertising, retail, and higher education. Now I do this work for a few select Lancaster County companies at a time, on retainer. Same experience, smaller bill, no salary or equity.

Based in Leola, working with companies across Lancaster City, Lititz, Ephrata, New Holland, and the surrounding county. The quarterly on-site working session is in person; everything else fits how you actually run your week.

  • 20+ years across enterprise tech — financial services, insurance, advertising, retail, higher education
  • Eight AI products live in production right now
  • Author of Concordance — AI-driven engineering governance platform we run on our own systems
  • HIPAA-aware: built ClaimsPeace and AuthPeace from scratch
  • Certified Agile Coach (ICP-ACC), SAFe Trainer, CSM, PAL
  • Lean / Design Thinking / Operating Model practitioner
  • Based in Leola, PA — serving Lancaster County and the mid-Atlantic
Common questions

Things people ask.

Honest answers to the questions every prospective fractional CTO conversation surfaces.

How is this different from hiring a senior engineer?
A senior engineer writes code. A fractional CTO makes the decisions that determine whether the code that gets written is the right code. The two roles are complementary — if your team needs a senior engineer, hire one. If your team has engineers but no one to set strategy, that's a fractional CTO.
What's the minimum engagement?
90 days. The first 30 are mostly listening; the meaningful output starts in month two. Engagements shorter than that don't deliver value — for either side. After 90 days, retainers are month-to-month.
Will you write code?
Occasionally and selectively — usually to unblock the team, prototype an architecture, or evaluate a technology. When the engagement needs real code shipped, build work scopes separately inside the relationship: targeted automation pilots ($10K–$40K, 4–6 weeks) or integration / storefront work sized to the job. The Fractional CTO leads it — you don't end up with shelfware.
Do you do agile or scrum coaching for our team?
Yes — coaching is how strategy becomes executable. Some weeks an engagement is heavy on strategy and vendor decisions; some weeks it's heavy on coaching scrum masters, POs, and engineering leads through retros, story mapping, refinement, and sprint discipline. Same retainer, different shapes. Your team has the customer knowledge and the technical chops; the coaching is the bridge that turns the roadmap into a team that can actually run it.
Can you facilitate product discovery or story mapping with our team?
Yes. The work isn't “we go do your discovery and hand you a deck” — it's facilitating your team through a structured process so they make the decisions and keep the muscle when the engagement ends. Discovery, journey mapping, zero-based design, MVP scoping with feasibility annotations — all of it fits inside a Fractional CTO engagement. You bring the people who know the business and the customers; we bring the framework and the facilitation.
What if our team can only meet evenings or weekends?
Engagements adapt to your team's reality, not the other way around. Some clients run their working sessions Tuesday evenings because that's when the floor is quiet; some prefer Saturday mornings for retros and refinement. Whatever cadence lets the team actually engage, the retainer covers. The point isn't off-hours as a discount — it's that the work happens when the team can do it.
Can you work with my existing engineers / agency / MSP?
Yes — this is often the right setup. The fractional CTO sets direction; the team or agency executes; the MSP keeps the lights on. I work alongside whoever's already in place rather than displacing them.
Do you take equity instead of cash?
Generally no. Cash retainers keep the relationship clean and the incentives aligned around your business outcomes, not my exit. Open to discussion if the situation is unusual.
What if my needs shift week to week?
Expected. The retainer covers ~10 hours/month on average; some weeks will be heavy (board meeting, vendor decision, hiring sprint), others will be light. We track time loosely and rebalance month to month.
How is this priced relative to a full-time CTO?
A loaded full-time CTO in PA runs $250K–$400K all-in (salary, benefits, equity, ramp time). The retainer is $54K/year — roughly 14–22% of that, for 15–20% of the hours, concentrated on the highest-judgment work. The math works as long as you don't actually need full-time. Below comparable fractional CTO retainers at the national level ($60K–$180K/yr range).
Can we start with a Discovery Call?
Yes. 30 minutes, free, no pitch. We'll work through what's actually slowing you down and decide together whether the Fractional CTO retainer, a defined engagement, or a different sequencing is the right next move. The call itself is useful regardless — an experienced outside read on a hard call is hard to come by.

Got a question? Write me.

Sometimes a sentence by email is the right starting point — context, a quick question, an introduction. I read every one.

terry@conestogastrategies.com

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Worth a 30-minute conversation?

No slides, no pitch. 30 minutes. Walk away with a clearer picture of whether a fractional CTO is the right next step for your company.

Book a Fit Call

Or talk to our AI receptionist now: (717) 366-9431