“Whenever you find yourself saying something for a second time (to a second audience or in a second situation), it is highly likely that you will send up saying it again and again in the future. To vastly improve the quality of the communication and reduce the amount of time that you spend communicating the information, write it down.

— Matt Mochary in “The Great CEO Within”, p. 22

I’ve been doing the fractional CTO (fCTO) thing for about two years now, and I get quite a few people who ask me about how I got things started. Given the rapid reduction in available software development-related positions, it makes sense that there are quite a few who are considering hanging out a shingle.

I enjoy discussing this with folks, but my policy on these things is that if I find myself repeating the same material, I should probably save myself and everyone else a lot of time by just writing it down! This is my attempt to do that.

Much of this advice on getting started is really applicable to anyone doing any kind of consulting.

How should I get started?

Have the experience.

I don’t have data on this, but I get the sense that the demand for fractional leadership has gone up since 2022. Supply has risen to meet that demand. However, a fair portion of the supply (of fractional leaders) has never actually been in a leadership position. When I ask clients why they choose to work with me, many of them have pointed at my experience as both a founder and a leader. A departmental manager at BigCorp might carve out a reputation as a team leader, but someone with very little (or no) prior leadership experience might find it difficult to find a toehold in a crowded market.

Find a niche.

One common issue I see with folks getting started is that they make no real attempts at defining where they can truly add value. I get that it’s tempting to do All The Things when you first get started - after all, you need to get paid and eat! If you specify a niche (industry, stage of company, B2B or B2C, SaaS or otherwise, or some combination of these things) you can start to figure out who you should be marketing and talking to. Speaking of talking…

Talk to a lot of people.

I get it, sales is hard (especially if you are an introverted engineer-type like me), but if you’re going solo then you’re also the salesperson.

The easiest way to figure out how many conversations you need to have is to take some notes from the SaaS sales playbook. First, figure out what your annual revenue target is. Next, determine what your average fractional engagement will net you. (If you’re just getting started, it’s going to be fuzzy math, but that’s ok! You can adjust this as you get more information.) Keep all of your opportunities in a CRM (HubSpot’s free tier is pretty good for a solo operation) and use that information to determine what ratio of conversations you have to close an engagement. Your sample size may be rather small, but again, fuzzy math is okay.

For myself, I’ve found that I need to have maybe 2-3 conversations a week with various folks in my industry. Those are not sales conversations, and they are very unlikely to end in an engagement. But if I’m having conversations with the right people, each meeting is a person who might know someone else needing my help. They could be a source for a warm lead.

Have some sample proposals (and deliverables) ready.

I have found it to be useful to have several different sample proposals on hand. It provides potential clients with an idea of how I approach engagements (clear terms, flat rates, etc) and makes them more comfortable with the idea of working with me.

Start with projects before going open-ended.

For me, fCTO engagements are completely open-ended. I’m only taking on two clients at a time, and generally they are a day or two (sometimes more) per week in, for which I am billing a weekly rate. However, that’s a lot to sign on for if you’ve not worked with me before.

To establish trust, I’ll often start a relationship with a well-defined project. Having a well-scoped project with a discrete (written) deliverable familiarizes clients with my working style (and me with theirs).

Keep the pipeline going.

If you pick up one or two projects, it’s easy to get so involved in them that you forget to keep talking to folks about potential future projects. When you finish the project, you don’t want to be in a mad scramble to find your next engagement.

What do not you like about being a Fractional CTO?

You do all the things.

Sales. Marketing. Accounting. Bill collection. As a solo practitioner, you do all the things. That eats into the time that you’ll spend doing the thing you love, but it’s part of the deal!

Staying fresh requires intentionality.

You’ll no doubt learn new things just engaging with clients, but to stay on top of industry trends (both technology and whatever domain you’re working in) you will have to allocate some time to ongoing self-education. It’s easy to skip this part, but don’t! Your continued usefulness depends on staying current.

You trade depth for breadth.

When you’re consulting, you rarely get to spend enough time with one project (maybe 3-6 months for most of my engagements) to go really deep. Instead, you get exposed to a broad array of industry niches, architectures, languages, and product categories.

There’s a trade-off here. I enjoyed going deep for 13 years (from first line of code to exit) with Stratasan. I also enjoy the variety inherent to consulting. Ideally, one could switch between depth and breadth every 5-7 years.

There will be juggling.

I take on no more than two fractional engagements at any time due to this. I also stress to potential clients that it’s fractional, not interim. This means I am not always immediately available, but I do clearly communicate my availability with all clients via Calendly.

What do you love about fractional leadership?

I love strategy.

As a fractional chief technology officer, I would presumably be working on engineering strategy. However, I find that when I start asking questions I often start edging into business strategy, which I love. There’s nothing more satisfying to me than a client asking me to sit in on one of their annual or quarterly strategic planning sessions!

I love the autonomy.

I get to choose the clients I work with, and I’m fairly picky about it. I only want to work with companies that I feel I can provide an unusual level of value (e.g., sticking to my niche of early-ish stage healthcare B2B SaaS). That makes the work both more satisfying to me and more valuable to my clients.

I love the security.

Assuming you are able to keep the pipeline going, there’s a lot more security in having six or seven ongoing clients (between fractional CTO, advisory, and project work) rather than putting all your eggs in one basket for a single company.

I love the variety.

I get bored fairly easily, so I love it when I can hit several interesting engagements in a single year. They will probably be in healthcare, but they could otherwise be completely unlike (different technology stacks, different business problems, different company cultures and problems they are facing). I thrive on this variety.

Parting Thoughts

If you have an appetite for it, I believe fractional leadership can be very fulfilling.

If you’re thinking about striking out as an fCTO, there are a lot of resources already out there to get you going. You don’t have to learn everything from scratch!

• Check out David Riastrick. He writes regularly about fractional CTO work on LinkedIn and elsewhere. He also has an email newsletter you can sign up for here.
• Check out the #fractional-cto-vpe channel on Rands Leadership Slack. They host a virtual coffee bi-weekly.

If you read all this and you still have questions, shoot me an email! I’m happy to answer additional questions, and I can update this blog post with more information in the future.

Photo by John Towner on Unsplash.