Services

I help companies when they need a little bit of extra technology/product muscle to get them through a transition period. Usually this takes the form of an Interim CTO/CPO, Long-term Fractional CTO/CPO, or a specific consultative engagement like due diligence or vendor evaluation.

Interim CTO / CPO Services

Sometimes a company may find themselves voluntarily or otherwise without a Chief Technology or Chief Product Officer. When that separation occurs, there may not be an internal heir apparent, and/or it may just be better for the company to take a more slow and deliberate approach to search. That’s where I come in. I can hit the ground running, spending a lot of the time with the existing team to make sure that they’re OK and can remain focused. Then with the team, I dive into the technology and product strategies, reconciling any misalignment between management’s expectations and the capabilities of the existing organization. As we develop and improve those areas, we start to work on the existing internal processes from idea incubation to code delivery.

Meanwhile, I can also help better define exactly what you should consider in any future candidates and conduct interviews (including of any internal candidates) to help you permanently fill the role. Sometimes this also involves making a few internal changes so that the new candidate can start with a healthier organization.

Fractional CTO / CPO Services

Many small to mid-size companies may not yet need the services of an experienced full-time CTO or CPO. It’s not unlike their periodic needs for a lawyer, or CFO (many companies start with a controller), Unfortunately, since technology and product requirements are not necessarily the forte of the founders, they either over-promote somebody who has less experience, hire an expensive external consulting firm (managing these vendors is a skill unto itself), or try a myriad of other things to try to make it work. What they really need is a few hours a week of somebody who can lend their expertise to their roadmap development, technology and architectural decisions, vendor selection and management, and internal team development.

If we are a good fit for each other, we can structure my services as hourly, 1/4 time (equiv to 2 hours a day), or 1/2 time (4 hours a day). I usually only take on work equivalent to 3/4 time which enables me to “burst” services for a client who has a particularly pressing or urgent issue that requires a lot of time and attention.

Consultative / Due Diligence

I’ve been on both sides of the investor <-> investee relationship and can help with either. I’ve raised lots of money (or helped companies get acquired), and guided investors towards good opportunities and away from potentially risky oneWhen evaluating an investment, my rubric covers 36 areas across the entire technology product organization, including the platform’s reliability (which includes scale, monitoring, alerting, etc.), usability, profitability, testability, supportability, deployability, and human capital.

Now obviously only very mature products will score extremely well across all of these capabilities, and some are more important (and expensive to fix) than others.

If you are on the investee side of this equation, the level of due diligence requested can range dramatically (depending in the size and structure of the investment firm, their experience and confidence with the leadership team, etc.). For larger investments or acquisitions, it may require discovery and disclosure of every piece of software running anywhere in the infrastructure, every single contract with every vendor, and a requirement for a complete audit of the source code to make sure there are no undesirable open source licenses applicable to any part of your technology stack. What you provide needs to be comprehensive, completely honest, and address every question that is being asked of you. Your in-house team may have the experience and capability to do this, or you may find that you simply don’t have answers, or enough available time to put this together and craft the procedures and policies that you’re going to need to implement as you take on this new investment. In either case, I can help 😀

David has been a go-to resource for technical diligence prior to decision making on investments. His knowledge, depth and understandings of technical infrastructure and wide purview of industry has been both insightful and very helpful. His investment recommendations have also borne out several years later with regards to which companies where going to be successful or not.

– Leib Bolel, Partner, Grayhawk Capital

Frequently Asked Questions

1. Are you opent to full-time work?

Of course, but the fit has to be really great for both of us. It’s really important to me that my job description doesn’t become “meetings and email.” I’ve been in organizations where too many people present the illusion of work by being in meetings without agendas for 6 hours a day, and eternal e-mail conversations / threads where nobody is willing to make a decision. Those cultures are exhausting and very challenging to change.

3. How do you juggle the scheduling challeges here?

Fractional work is generally pretty easy to manage, especially because I have clients in multiple time zones. The timing for an interim gig can be a little trickier, but the best thing to do is to contact me and see if the timing aligns.

2. Do you accept equity compensation?

Not at first, because an over-willingness to offer equity is usually a sign that the owners either can’t raise money easily, or aren’t yet sure if they are going to be successful. It’s also too difficult to gauge the value of equity until I understand the cap tables and have a sense for the organizational capabilities. After getting to know each other for a month or two, we can certainly talk about some combination of cash and equity.

4. What do you do when you’re not engaged with clients?

I write, travel, and have a few projects that I pursue when time allows.