Where can I find a REAL CTO?

Andrew B MacDonald Founder & CEO B2BizMeet (formerly VendorAir). Entrepreneur, Sales Leader, Dartmouth

May 19th, 2019

Hello CoFounders. I'm stuck where to go next for my final team hire so looking for advice. I've onboarded my Pres/COO and CMO. We've been heads down refining the vision, we've renamed, rebranded and redone the deck. I've realized in the last month that I need a key CTO onboard now vs later. My platform scope is beyond what I can develop against with Freelancers to get to MVP. I've done a lot of networking to locate this elusive person, and now maybe ready to try Freelancer sites? I've heard mixed reviews. I've used Freelancer.com and looked into TopTal, but I'm looking for advice because all those sites are selling their talents and it's possible to get wrapped into an individual who can't handle development of a complete platform solution/vision. I also need this person to be in Boston (where I'm located) and most of my network leads back out to SF/Valley. Most advice is the same (go to meetups, look at Grad Programs, dive into Incubators), so maybe that's where this person will turn up. Any advice from CoFounders who've hit this hurdle before? I've been gaining a ton of confidence based on Seed conversations, but it's clear this hire is key to move forward. I'm feeling those entrepreneurial nerves again because my first two hires have been spot-on. I don't want a misfire to disrupt the flow we're in. Advice? Best, Andrew

Michael Wojciechowski

May 23rd, 2019

If you are onboarding Pres/COO, CMO and now look for a CTO, before even having a validated product, than as a CEO I believe you are more interested in titles than getting your product out the door. Before you validate, you have nothing. No company, no C-level - you have nothing. What you need in the super-very-early stages of your startup is to roll your sleeves up and do all the business part yourself and get a person who is your exact counter-part but technical - so they get to complement your non-technical part. Sorry about the bluntness - but if you take this advice, it will save you lots of grief down the road. I wish you all the best!


PS. My CTO is an ocean across. It is someone whom I have hired before and whom, after 7 years of sweat, blood and tears together in the trenches with me working on contracts, proved they're the right person for the role.

David M

May 29th, 2019

@Michael, what you state may have application in some scenarios but by no means all. If you are making 10 cent widgets then perhaps your comments hold water. But when you are working on putting together a company that needs a significant raise, having a competent team that includes a CTO, COO, CFO, CEO has nothing to do with titles as you suggest but the experience behind those titles. And that experience is precisely the first thing investors look to, not product validation proving you have sold a few thousand units in a sea of start up products that prove initial validation but often fizzle because they don't have the executive leadership to manage and scale that validation. In a perfect world, yes you have both, but again if you don't have the team that can scale a business, you just have another widget that will never reach top shelf placement.

David M

May 21st, 2019

Andrew, don't you love on Co-Founders Lab how everyone makes a hundred assumptions based off of a paragraph? Unreal. I will take your word, CEO's word, and answer the question rather than assuming you do need this, don't need that, aren't ready for this... so I can puff up show off how much (or little I know). If I were in your situation, I would look to the companies you admire, who have had success, and are in a similar or the same market. I would then research their CTO's as best you can. In many successful companies, C level founders/early employees work with the company to a certain point and then branch out and leave. You may be able to pick up a great CTO who is looking for his next start up success. Some will chime in "But they will want a bigger portion of equity." And to that I say "Great! Give it to them, and build with a leader and a proven track record." Another option is to email the CTO's of those companies and approach them with an "I admire your company/product,,etc. I have a start up (Then give a positive non inflated assessment of why this person should be reading your email). Humbly ask if they know of any up and coming CTO's who might be looking for this type of challenge. Worst case scenario, they say no...best case scenario you gain a future collaborator or board member. All of your contacts and needed ins are out there if you are willing to do the research. I never use cattle call websites, because I prefer to make approaches with far more research and precision. But there may be some out there...I just don't know of them.

Mitch Harris Co-founder/CTO of QPID Heath

May 19th, 2019

1) To prospective CTOs, you have to be clear about what you want at this stage. Do you have an MVP already or just a few mock screens or somewhere in between? Do you want this CTO to be the chief cook and bottle washer (sysadminning, database, backend and frontend development), the tech manager of dev hires, or the manager of and specs creator for the TopTal consultants. Or do you want a CTO that is the technical vision who delegates to tech hires (the classic definition of CTO)? Also, be clear about scope (how much needed to be built, how many clients expected to service).

2) CoFoundersLab is intended precisely for your situation, to help find people interested in situations like yours? Trawl through their search page, restricted by location and other things and contact them.

As an aside, I find TopTal is better than others (the people are pre-vetted for skills). If it is a big project, they also have people who can do project management for you (if you have the money for that). Your tech person will still need to do a lot of work creating specs for them (or any consultants) though; you can't just hint at them that "It'd be nice to have feature X" and expect it to be done how you like.

Tony B All knowledge is self knowledge. Keep learning. Stay hungry.

May 19th, 2019


Let me come at you from a different angle. Instead of just looking for top established contenders, you might consider creating your own CTO. It may not be as arduous as you think. If the person needs to be local, try your local technical staffing agencies. I believe Addison Group might have a presence in Boston, but also be open to remote talent. Your looking for a seasoned and established senior developer and/or technologist with good problem solving ability and strong confidence in their tech toolbox. I hired a senior developer over a year ago to groom as my replacement as CTO in a project I've spent over 9 years on and it worked out very well. They weren't as rigid as an established CTO may have been and that worked out to my advantage. They had a strong grasp on their skill set and strong ability to research and problem solve; yet didn't need micro managed.

You are correct to be concerned about the freelance sites, however they are still worth some effort if you've exhausted all other avenues. It will take some serious filtering, but there are some good talents there. Cheers!

Steve Owens Startup Expert

May 20th, 2019

Missing a lot of information to make any definitive recommendation, however, it sounds like your still in the market validation stage. I would not hire any full time employees at this stage - in all likelihood, they will not fit the company a year from now when you have pivoted 6 times. Even if you do not pivot, the likelihood of getting an "A" player to take a startup job with all the inherent risk is almost zero - and that assumes you can provide a competitive compensation package.

There are plenty of product development companies that specialize in helping startups and the best one is in Boston. They have a whole team of people and CTOs with processes in place and reference designs. This will be a lot cheaper than developing your own team, and allows a lot more flexibility.

jFaleiro Founder @ Optera AI + Quant Strategies; Co-Founder @ DOCTRI Analytics. Computer Scientist, Trader

May 22nd, 2019

Your question misses a few critical details so I will have to go with a few assumptions.

Needless to say technical talent is scarce. Scarcity pushes people to look for unrealistic workarounds. Some times workarounds take the shape of off-shored teams with dozens of pigeonholed, inexpensive programmers. Some other times workarounds take the form of a do-it-all local CTO, struggling to engineer your vision by himself.

You might not need that one real CTO, mainly because in all honestly a "REAL CTO" is a fallacy. Modern business and technology should be one. Founders should be tech-savvy. If you are having difficulty to get to an MVP, which skill exactly are you missing? Qualified programming skills? Proper agile methods? Engineering/architectural directions? Vision is still adapting?

IMHO your main answer lies somewhere around the answer to these smaller questions.

I hope this helps, good luck!

Ian Shafer Co Founder at Anthology

May 19th, 2019

It sounds like you need somebody to take your vision and make it a reality. You don't need a CTO in the traditional sense of the title. You need a strong engineer with experience across the full stack (front-end to backend, designing to maintenance, building to deploying, data modeling to serving, etc.). Yes, this can be tough to find, especially if you require experience in all facets from the start (a good engineer can learn what they need to know).

You could look at junior engineers with ~4 years experience working at a reputable tech company. By this time they've learned a bunch and may be ready to jump ship and be freed from the shackles of the corporate world. Your selling point would be the responsibility and opportunity that you are offering.

Paul Garcia marketing exec & business advisor

May 21st, 2019

This is a classic case where title inflation is getting you into trouble. There's probably no reason that you should be giving out C-level titles. Being first does not qualify someone for a c-suite title. And in seeking a CTO, you're holding a lot of baggage for what that title is supposed to mean. It can also get you into trouble if you are looking for investors and they discover that your team doesn't actually meet the intended definitions of what those c-level titles mean to the corporate world.

Instead of focusing on filling a title role, it is much more effective to search for someone who has the specific work skills that will move your enterprise forward.

I'm glad you have found some spot-on hires so far. My guess is that you approached these people based on meeting specific talent requirements and not based on their previous title. I'm also here in Boston and there are plenty of technically capable people who are able to be the administrator of platform development, business folks, not just an experienced programmer. And you can probably find some of those who would be interested in a startup environment and the industry you're facing.

What often happens when looking for freelancers is that you end up focused on what the person can do for you, not what you can do for the candidate. When you're in a market rich with opportunities, ticking boxes for talent isn't the most effective way to find a new employee. What works better long-term is communicating how your opportunity benefits the candidate and attracting them to you instead of you hunting for them. This is internal marketing, your employer brand, what it's like to be a part of your company, how you solve problems and work together. It's not about free coffee and a great location.

My advice is to rein in your attempt to satisfy a role, and break the work into more discerning tasks. What is this person's daily life going to be like? When do they come in? With whom do they interact? What is the first thing they do each day? How much of their time is spent doing what kind of work? What is their problem-solving method? How much independence should they have? What level of authority do they need to get the job done? Where will they go when they have issues? What decisions are they making on a daily basis?

These characteristics are much more useful in finding a candidate who is a match than listing technical skills and previous experience. Remember that a resume can only tell you what someone else asked a person to do, not what they're capable of doing.

Good luck!

Nicholas Cody Product Lead Manager | UI/UX Enthusiast

May 25th, 2019

Hi Andrew, i hope this would give you another angle. Instead of a CTO i’d suggest you’d find for a CPO instead. Find a CPO with a strong technical background (doesnt have to be dedicated programmer, but should be able to understand system design and other technical flows) By having a CPO you’d have another brainstorming mate (business wise, experience wise and tech wise) and he/she should be able to understand your objectives and vision, translate it to product requirements, build the prototype (hi-fidelity screens) and once all ready i’d suggest you’d find a freelance developers lead by the CPO That should give you a detailed and agile plan for your MVP. Hope that helps!