I’m a founder-type, builder, and technology executive since the mid-00s.
Throughout my career I’ve worked in a part-time, fractional, interim, or advisory capacity to founders, SMBs, and enterprises through my firm greyworks.
This was often on-top of my primary focus. These days, it is my focus.
My sweet spot are technology companies
This includes companies that are already technology-enabled as well as those that are tech-aspirational beyond “basic IT”.
Especially if you find yourself having build vs. buy conversations at the leadership level, call me!
going through transformational moments, whether it’s the company’s founding, early/mid-stage pivot, and/or growth investment through a financing round.
If I can be helpful, do please reach out using the e-mail address at the very bottom of this page.
Services
I’ve titled this page “Fractional Executive Services” as it’s becoming industry term-of-art, but I’m also comfortable with other arrangements.
| My Role | My Partners | Strategic | Tactical | Operational | Usual Time |
|---|---|---|---|---|---|
| Fractional | Leadership | ✓✓✓ | ✓✓✓ | ✓✓ | PT/Ongoing |
| Consulting | CEO/CXO/VP/Dir | ✓ | ✓✓✓ | ✓✓ | PT/Limited |
| Interim | Leadership | ✓✓ | ✓✓ | ✓✓✓ | FT/Limited |
| Advisory | Board/CEO/CXO | ✓✓✓ | ✓ | As-needed |
Table Key
- PT: Part-time
- FT: Full-time
- Strategic: Long-term planning
- Tactical: Short-term execution
- Operational: Day-to-day management
Number of checks (✓) indicates relative focus within each role.
Currently On-Offer
Fractional Leadership
In the way you might have a lawyer on retainer, a Fractional Leader is a long-term, part-time executive who can help you make good hires, good design choices, and good use of spend, without the full freight of a full-time executive.
This often means you can afford to make 2-3 more full-time hires than you would be able to otherwise—and with proper oversight!
I’ve held the following roles in the past in a full-time, part-time, or interim capacity; or, as core to my larger remit.
Chief Product Technology Officer (CPTO)
This is what I do most of the time.
As the name suggests, it’s a blend of CTO and CPO: a CPTO is a technology executive who builds a product-led technology organization that integrates well into company operations, keeping the core business and its customers top-of-mind.
I usually shorten this to “CTO” as “CPTO” is a mouthful.
This is sometimes called “Chief Digital Officer”; but given my experience and skillset, I prefer the “Technology” moniker over “Digital”, as the latter is often associated with marketing- and sales-driven organizations.
Chief Technology Officer (CTO)
Ignoring any product responsibilities (see CPTO above), a CTO is often responsible for the technology: the stack, the team, and the execution strategy. This is often a more technically-focused (“how do we actually build the thing?”) role than the CPO role (“what should we build?”), but the two are intertwined. (Major problems happen when they’re not.)
This is why depending on the organizational topology and maturity, the CTO may also own Product. Additionally/alternatively, the CTO might own the data (CDO), security (CISO), IT (CIO), and/or infrastructure functions.
Chief Product Officer (CPO)
Often called Chief Strategy Officer (CSO) or Chief Innovation Officer (CiO) in some organizations, the CPO is responsible for the product strategy and roadmap. Depending on the organization, the CPO may also own design, user experience, and/or research functions.
This role requires a deep understanding of the market, the customer, and the technology, and is often the bridge between the business and the technology functions. It is also a role that relies heavily on soft skills and influence, as the CPO is often responsible for aligning the entire organization around the product vision.
Chief Information Officer (CIO)
In companies that buy more than they build, this is a critical role. As I often work with technology companies, this role is often folded into the CTO roles; but in larger organizations, the CIO is responsible for the IT function, including the infrastructure, security, and compliance functions.
I do not usually do this work independently of the CTO role, but I can recommend some excellent candidates.
Chief Information Security Officer (CISO)
The CISO is responsible for the security of the organization, including the security of the technology stack, the data, and the people.
Like the CIO role, I do not do this indepenedently of the CTO role. I can, however, help technical leaders on a project basis to improve their security posture.
Chief Data Officer (CDO)
The CDO is responsible for the data strategy of the organization, including the data stack, the data team, and the data governance.
While I have run data teams in the past, I do not typically do this work independently of the CTO role anymore… unless Data is a first-class citizen of an organization (e.g., a data company) and there is no CTO.
Non-Fractional Reasons People To Come To Me
Phrased as questions:
- Do I need a technical co-founder?
- My CTO just quit. Can you help with a transition?
- I hired a development firm but it’s not working out. Can you fix it?
- What technical diligence should I do for an acquisition?
- How do I know if my product and engineering teams are any good?
- What tech stack should I pick for my startup?
I encourage you to ask your favorite generative AI tool (e.g., Anthropic, ChatGPT) as a starting point—they’re great assistants and I use them daily. When you get stuck, give me a shout as there’s limited intelligence in that “AI”. (It’s very fancy, very cool applied statistics… albeit not intelligence. I digress.)
Interim Leadership
Do I need a technical co-founder?
Maybe! Or, maybe not.
In the not-so-distance past, entrepreneurs sans technical co-founder had greater difficulty raising venture money than with one. These days, there’s more flexibility (although raising money is still very difficult).
A Fractional CTO is often a thrifty technical co-founder: you get all the wattage of an experienced technical executive at a fraction of the dollar-cost and deep discounts on share allocation (if that’s even applicable or appropriate given the arrangement).
Fractional Co-Founder. Consultant will serve as the technical co-founder, reporting to the CEO, for a period of 12-18 months, starting at 20 hours/week and scaling back to 8 hours/week on a mutually-agreeable schedule. Consultant will hire and manage the product and engineering team responsible for building the initial go-to-market effort, as well as support company fundraising and budgeting.
A technical co-founder will help you make good design choices and good early hires (direct or via development shops), allowing you to get to market more quickly and reliably than relying on external vendors with mixed incentives. (Fractionals are paid for their time, not on your spend.)
My CTO just quit. Can you help with a transition?
In short: yes.
CEOs: there may be a temptation to elevate the highest-ranking or high-performing member of their surviving team to fill-in until a replacement is hired. I have never seen this go well for either the company or the temporarily-elevated employee. There may also be the urge for you, the CEO, to assume the CTO’s responsibilities until a replacement is found. Unless the CTO already had a fully-stacked deck of high-performing managers (or managers-of-managers) as direct reports, this also tends not to go well unless the CEO is also technical leader and has the bandwidth. This is uncommon.
Instead, I recommend hiring, either:
- a Technical Advisor who can help plot a course of action, and/or
- an Interim CTO who is a decent fit for the team.
This role may be fractional or full-time, but it buys time to find the right long-term hire. (I recommend starting with the advisor.)
A strong advisor and/or Interim CTO can even help recruit their replacement and ensure your finalists will be a good fit for you and the team. This is very, very difficult for a CEO to do alone, particularly with the incoming capacity gap from the departing executive.
Depending on my availability and fit for your org, you can hire me or I can recommend a suitable candidate from my network.
Sample engagements:
Technical Advisor. Consultant will serve as Technical Advisor to the CEO, for approximately 5-8 hours/week for 2-3 months (or longer, as needed). Consultant will evaluate capabilities and operations of the product and engineering teams, helping the CEO decide on the best course of action and providing guidance throughout the transition. Consultant will also help interview candidates and onboard the incoming CTO.
Interim CTO. Consultant will serve as an Fractional CTO (20 hours/week) on an interim basis (3-6 months), reporting to the CEO and the Board of Directors. Consultant will assume responsibility for the continued performance and operation of the product and engineering teams, providing a management layer to ensure members of the team are continually well-supported until a full-time CTO is onboarded. Consultant will also help interview candidates and onboard the incoming CTO.
I hired a development firm but it’s not working out. Can you fix it?
Yes.
(Next time, hire someone before you contract out your software development, especially if you’re not technical yourself! Except in special cases, I also recommend ensuring that your CTO/CPO, fractional or otherwise, is not packaged with the development firm you hire—keep your controls separate from the software development execution.)
This happens more often than people talk about. Candidly, it is often not the development firm’s fault; but, rather a misalignment of expectations, communication, and/or incentives.
Sometimes, though, dev shops have taken you for a ride!
For my part, I can help make sense of the situation and provide a plan and ongoing support to get things back on track.
Due Diligence
What technical diligence should I do for an acquisition?
For mergers and acquisitions (also lifted from a previous offering):
Technical Diligence. Consultant will serve as firm’s technology investment/M&A advisor, retained at 30 hours/month.
Consultant will analyze and report on acquisition targets’ technology organization’s maturity, including: software development life cycle, code quality, and technical obligations (debt); will also identify existing and emerging risks, including compliance and security concerns.
In cases where system integration is anticipated, evaluate feasibility and scope.
How do I know if my product and engineering teams are any good?
As the Product and Engineering function is often the most acutely felt barrier to growth, it’s always useful to get an independent evaluation on how the team is doing. Sample offering:
Technology Maturity Audit. A thorough assessment of both your technology team’s capabilities and your current infrastructure and assets against benchmark. Conducted over 2-5 business days for startups < ten FTEs (and 2-4 weeks for larger companies) and culminating in a written-report that synthesizes findings, you’ll gain insights into your company’s technology function along with actionable recommendations to improve the team’s productivity, output, and happiness.
What tech stack should I pick for my startup?
This is often, quite literally, the million dollar question.
If you’re unsure of a path, would like to validate a chosen path, or need help changing the path, I highly recommend soliciting unbiased feedback whether it’s from me or another qualified tech executive. Too often do I see well-intentioned “we need to build an MVP that also ready to scale!” efforts that lead to heartbreak, a heap of ashen currency, a run-down time-clock, and a pile of regrets.
Consider hiring a fractional technical co-founder to navigate through this.
Other Services
Some smaller deliverables I’ve knocked-out on a project basis—usually for peers—when time allows.
Hackathon
I’ve run a few of these, both technology-wide and company-wide. They’re highly impactful to lateral thinking and (more importantly) building camaraderie among teammates, especially those who don’t get to work together often.
IT Strategy and Business Software
Especially at the early stages, CTOs often double (or triple) as CIOs, CISOs, and CPOs. (That’s information, information security, and product.) Sometimes this is called “Information Technology”, “Enterprise Technology”, “Business Software”, “Internal Tools”, and the work is often partnered with Operations.
This project is often about buying, installing, and training on a vended software stack; usually includes some minor integration work. Occasionally there’s an opportunity to build custom, but rarely.
Operational and Compliance Program Support
I’ve helped stand-up several compliance programs for multiple companies, setting “land speed records” for SOC II Type 2s… often the gateway requirement for US-based companies selling to enterprises.
Evaluate current [Tech|Dev|Sec]Ops maturity and develop a go-forward plan.
Provide technical operations guidance and leadership for compliance, trust, privacy, and safety.
Technology Recruiting Playbook
See Interview Circuit for my framework.
Develop a comprehensive technical hiring playbook tailored to your company’s needs, ensuring an efficient recruitment process.
The playbook will provide a structured approach to identifying, attracting, and assessing talent and fit.
Deliverables often include:
- Org chart target
- Job descriptions
- Structured hiring interview process
- Team training