Fractional CTO

Since the early 1990s, I’ve been a part of 50+ startup companies in various roles, and have informally advised 100s of other startups.  Through these experiences, I’ve become increasingly convinced that early to mid-stage companies need to stop being locked into full-time executive hires (especially CTOs) and in most cases use fractional hires and/or advisors.

Almost all software-enabled startups do not require a full-time CTO, and their CEO should be using a fractional CTO and/or technical advisors.

I get at least one email each week from startup CEOs who are looking for a CTO. Well, let me be more specific – startup CEOs have varied specific situations, but the two most common are:

• I’m just beginning, and I need to find a CTO to build my MVP and to help me get investment.
• I hired (or partnered with) a CTO to build my early versions, and I need help because the technology is a mess.

Take a look at these two common situations. What do you notice? They are the before and after picture for a lot of startup CEOs who didn’t have the right people involved. The CEO who starts out looking to hire a CTO to build their MVP often turns into the startup CEO with a technology mess. Why is that?

A full-time CTO in an early-stage company?

To start to answer this, let me take you back to one of my early experiences.  I was an early hire at a couple of software startups in a senior software role.  While my title implied executive, the reality was that there was some early strategy work but then I was quickly spending all my time being a team lead and coding.  I was really good at both leading developers and coding, but my passion was the strategy. Within a month of being hired, my time was roughly 10% strategy and 90% development. 

What do I mean when I say strategy? It’s answering the following kinds of questions:

• What should we build to get the biggest bang for the buck?
• How much will it cost to build what we need to build?  How can I control costs, but effectively get stuff developed?
• How can we phase development to balance cost, features, risk, etc?
• Given likely market changes, how will we design and build so that the systems can respond to marketplace changes?
• What technologies will we use?  What existing systems will we leverage, what programming languages, software development methodologies, web application frameworks, revision control systems, etc.?
• Other integrations?  Security?  Scalability? 
• Who will build it?  An in-house team?  Or will we outsource?

There are many more of these questions that you can find in Startup CTO or Developer.  

These strategy questions are critical to ask if you want to find good answers.  When I first started each of those roles, I needed to spend time upfront getting the right answers to strategic questions.  But once you start to get those answers, the bulk of the time (and money) needs to be spent on getting things built. 

In talking with a lot of fellow CTOs, they’ve had the same experience in early-stage companies.  Simply put, early-stage companies don’t have a full-time CTO role. Instead, they have need for getting good answers to these strategic questions, and then they need a team lead and hands-on coder, and perhaps some number of other resources.

Before and After Mess

So let me go back to the before and after picture for the startup CEOs:

• Before: I’m just beginning, and I need to find a CTO to build my MVP and to help me get investment.
• After: I hired a CTO to build my early versions, and I need help because the technology is a mess.

The startup CEO who doesn’t get help from someone like me, and is going around saying they need to “find a CTO,” is looking to find an individual who is going to do strategy work (hence the CTO title) but is also going to be the team lead/developer.  The reality is that the CEO will be unlikely to get any CTO who has good strategy skills who will also be willing to sign up to be the team lead/developer. Instead, they are highly likely to find someone who is mainly focused on development, and they will be given a title (CTO) that implies strategy knowledge and skills that they don’t have.  What happens?

Look at the “After” picture.  Even if you are lucky and are able to find a developer who has good team lead and development skills, because of the lack of strategy, very likely what will be built is the wrong product, technology, and team.  You are left with a “technology mess,” and will start to hear a lot about technical debt and refactoring. New technical people will talk about re-architecting or even rebuilding.

Where did these CEOs go wrong?  They asked the wrong question at the very start.  And it’s not at all obvious, because you ARE looking to find a CTO.  It’s just not a full-time CTO – it’s a Fractional CTO and maybe a technical advisor or two.

How Does the Fractional CTO role work?

Let me go back to my personal journey.  So it’s the midst of the dot-com boom (later to be known as the “dot-com bubble”).  I’ve been in a CTO role at a couple early stage companies that turned out to really be a team lead/developer role.  I’m meeting lots of startup founders who have some funding and really “need to find a CTO.” So, in 1997, I decided to shift gears and agreed to be a fractional CTO for 3 startup founders.  I would do the strategy work - ask and find answers to the key questions. Then I would get the right team, technology and process in place. Basically, I am agreeing to be the CTO of all 3 of these startups, but at the same time.  

Of course, to be more accurate, the work I did was staggered out.  The biggest chunk of work as a fractional CTO is at the start, and then it settles down.  Even with them staggered, there were some fun challenges for each. One company was an event photography business that was transitioning to delivering services online; another was an art archive software becoming a internet-enabled SaaS company.  These presented some interesting strategic challenges, especially back in those days.

In each case, it worked well to be a fractional CTO.  I would make sure we were building the right product and define the technology strategy.  I would figure out and help find the in-house/outsourced teams. Then I’d work with them to make sure we were building the software well, and work with the rest of the business to iterate and adjust.  Really, it’s what you would want from a CTO. But rather than a full-time CTO, I was doing this on a part-time basis.

When does the fractional CTO role end?  It varies based on the company. With eHarmony, I was the fractional CTO from concept through to when they raised $110M - a period of four years.  It didn’t make sense for eHarmony to have a full-time, in-house CTO during that period of time. Once they raised $110M, then it made sense for them to have a full-time CTO and in-house development team.  Until then, they needed to prove key metrics and keep burn low.

The other common scenario is thinning down the role based on growing in-house talent or bringing in the right person who can bridge VPE and CTO needs.  Sometimes I will take on a small consulting role to help the VPE and CEO in an on-going basis, but I won’t need to spend many hours. When this can be an in-house resource, I always feel an extra bit of pride for a successful collaboration with them to reach that state.

Review and Turnaround Fractional CTO

Over the years, my Fractional CTO roles have been increasingly when organizations have an existing tech team and and some technology challenges.  The executive team sees the product is struggling with bugs or performance, the tech team isn’t producing at the needed rate, and they are missing lots of deadlines.  Basically some variation of “I feel like we should be doing better.” 

It’s generally a business executive who calls me, and they often start by saying they don’t really know the cause of the issues, but they also have lost confidence that the tech team can solve it on their own.  

This situation sometimes occurs because early in the life of a startup, the bulk of the work is development - so it’s natural to hire or outsource for development.  Often you are bringing on relatively more junior resources. And they are optimizing to get product shipped quickly. You said MVP right? It’s minimum long-term architecture in most cases.  Unfortunately, the same relatively junior resources are going to be challenged when it comes time to somehow get from a messy, fast moving initial period into a more stable state that will support customers.  These are some of the hardest challenges. The plane needs to keep flying and we need to change a wing. Quite often the current resources are a great part of the longer-term picture, but they lack some of the skills now required of them.  

One of my favorite parts of being a fractional CTO is the opportunity to work with up-and-coming talent to help them learn and adapt to the new skills required as the organization and tech transitions.  Many of us technical people grew up from individual contributor to various management positions, but just have not been given much help in growing our skills and knowledge along the way.  

So as I come into a new organization, I’m working closely with the business and team to determine what the team composition needs to be, where there are gaps, what new team members are needed.  For existing team members, I enjoy rolling up my sleeves and spending time coaching and developing. For places where we need additional talent, I define positions and collaborate on recruiting, onboarding, and retention techniques. 

Interim Fractional CTO

In this case, a CEO will call because they just got 2-week notice from their CTO or plan to let them go very soon. It seems to be coming up more often recently, and it’s a slight variation of the turnaround situation.  There’s an immediate gap created in the organization. Overall the technology team seems to be doing okay, but we don’t want to lose momentum. Maybe there’s someone who is a possible internal candidate, but who lacks some skills.  There’s a question of whether that person can fill the senior-most role. Or if there’s no one internally, a fractional CTO is a great way to bridge the gap to the new CTO. 

Of course, once you get into the specific situation, there are often more issues to figure out.  Quite often, the CTO leaving or getting let go is an indicator of other problems. So while you hope that an interim situation will mostly be maintaining the current situation, sometimes there are turnaround aspects.  At a minimum, there’s need for defining the new CTO role, helping with recruiting, and making sure the team stays focused in the interim.  

Getting Started with a Fractional CTO

As a CEO, it can be a little bit intimidating to get going with a Fractional CTO.  What does the organization actually need? Is this person qualified to do the job? How will they be working with the existing/new team?  What will it be like working with them?

Let’s go through what my initial process looks like and then come back to these questions.  Typically, I’m introduced to a CEO through a fellow-CEO (often past clients) or via investors.  We have a couple of initial conversations to assess the situation together.

If it’s a brand new product build, then the questions I have are pretty much in: Free Startup CTO Consulting Sessions. I want to know about the business, product, budget, key milestones, etc.  

If it’s not a new product build, then I’ll still want to know those things, but I’ll also ask about:

• Key pain points for the organization
• Key technical team leaders/members. Who will I be primarily working with? Are they aware of the concern and that you are looking for help? This is often a great first conversation.
• Existing and planned technical team shape and composition
• Product leadership

From this information, I’ll be able to formulate a picture of what the organization needs.  In some cases, I will talk to a CEO and realize that it’s just not very clear. In that case, I may need to have an initial meeting with a couple key players.  Even this next week I’ve got meetings to a CTO and CPO that’s exactly that kind of situation. But most of the time, I have a fairly clear picture of what it would look like for me to take on the Fractional CTO role.  If there’s a deeper initial technical review required, I’ll know that as well and likely will suggest some resources to help with that.

From there, I will write up the initial and on-going process and work effort, will size it, and then will provide an estimate.  There’s almost always more upfront cost as I get up to speed and then it thins out over time. But my philosophy is not to ever have surprises around cost, so I’m clear on it.  And as a Fractional CTO, my costs will be a fraction of the cost of a full-time CTO, freeing up budget for individual contributors who are the real engine of a technical team.

Let’s go back to the challenges that the CEO is facing as they look at potential fractional CTOs:

• What does the organization actually need?
• Is this person qualified to do the job?
• How will they be working with the existing/new team?
• What will it be like working with them?

For each of these questions, the CEO should be able to get answers through our initial conversations.  We get pretty deep in those conversations where we are actually working together to define aspects like how to communicate with key senior tech team members. Again, I may even have initial conversations with other team members.  The CEO should also ask about prior related engagements that relate to this engagement.

Conclusion

If you are a CEO, I hope that you have been at least convinced to explore this.  I’m always happy to talk about this and explore what might make sense for your organization.  Send an email to me (Tony Karrer): akarrer@techempower.com

Top CTO Challenges for 2019

The LA CTO Forum recently conducted a survey to find out what our Chief Technology Officer (CTO) members saw as their biggest challenges heading into 2019.
We received over 250 responses that provides a pretty good insight into the top CTO challenges.

The rating scale was 1-5 with:

1. Not a challenge
2. A small challenge
3. Somewhat a challenge
4. Definitely a challenge
5. Keeps me up at night

We provide both an Average and a Scaled Rating that gives much higher weight to 4s and 5s and discounts 1s and 2s.

Here are the Top CTO Challenges for 2019 sorted based on scaled rating - biggest challenges first.

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Challenge	Average	Scaled
Recruiting, Hiring, Sourcing and Onboarding	3.53	0.48
Appropriate Security for my Organization	3.49	0.47
As a tech leader, where do I spend my time	3.45	0.46
Personal Career Planning	3.15	0.40
Business Metrics for CTOs / engineering	3.20	0.39
Motivation of engineering team	3.21	0.39
Tech Vision and Tech Roadmaps	3.19	0.38
Talent Management, Career Development of team	3.24	0.38
Organization and Structure of engineering team	3.15	0.37
Managing Technical Debt	3.18	0.36
Executive Presence	3.06	0.36
Architecture Decision Making / Reviews when you are not the architect	3.11	0.35
How to find, explore and choose new technologies	3.03	0.34
Capacity Planning and Resource Forecasting	3.06	0.34
Testing / Test Automation	3.05	0.33
Technical Metrics	3.04	0.33
Relationship with CEO	2.88	0.33
Relationship with CxO Peers (Marketing, Sales, Service, Operations)	2.88	0.31
Management of DevOps, Site Reliability Engineering	2.95	0.31
Collaborative Decision Making	2.95	0.31
Integrating Offshore, Remote and In-House Engineering	2.81	0.30
Effective Agile Management, e.g., Flow Efficiency, Sprint Boundaries	2.90	0.30
Working with Product Management	2.85	0.30
Delegation & Prioritization	2.87	0.29
Sourcing and Managing Remote engineers	2.77	0.29
Engineering Management Team (Direct Reports)	2.82	0.28
Sourcing and Managing Offshore engineering	2.62	0.26
Complex Technology Partnerships & Vendor Negotiation	2.68	0.25
CapEx/OpEx optimization	2.65	0.25

It's not surprising that Recruiting and Security are at the top.  I was a little more surprised by topics such as "Where do I spend my time" and Personal Career Planning near the top.

Similarly, I was surprised that "Working with Product Management" and "Effective Agile Management" were not bigger challenges for most members.  These have perennially been a much bigger challenge.  Maybe we CTOs are improving.  

We are looking forward to interesting sessions in 2019 on this topic.  I would expect that we'll see some of these discussed on CTO Universe as well.

Anything surprise you?  Or something that we missed?

Finding Startup Developers - First Email Contact

Here is the most recent version of an all too common email inquiry from a startup founder.  I've removed the two words that described the market - otherwise this is verbatim.

I'm working on a start up idea in the XXX market with my partner and we are currently looking for full stack developer to join us as a technical co-founder. We have been reading about the LA CTO Forum and we thought it would be a great place to find him/her.

Please let me know if you can share this information with your members. 

I've written before about having an Initial Conversation with a Potential CTO.  That post and How to Find Programmers for You Startup - a Field Guide both lay out a lot of the tactics that will prepare a founder for important early conversations.

The above email is SO BAD that I feel compelled to treat this email as a special case so maybe I can help other founders before they send this email.  Or at least send them a link to this post if they have already sent something like the above and let them know what I would have wanted instead.

Homework

I don't think that this founder has looked at my blog or my background.  If they had read either of the above articles or the 10 other on my blog, then they would have sent me something else.  So, why should I spend time if they've not spent time?

Startup and Founder Backgrounds

This is a cold email. I don't know the individual or his partner.  And I don't know anything about the business.  If you want me to take you seriously, then get me interested.  What background do you have?  Why is this a great startup?  What have you done so far?  This should be your elevator pitch. Get me interested.  And please include LinkedIn URLs so that I can easily find your background.

Of course, this needs to be "elevator size" - 3 to 4 sentences.  Otherwise, I won't get to your ask.

Think About Your Ask

Likely many startup founders, they want help getting their startup concept built.  The way they expressed it "technical co-founder" is code for find someone who will work as an Equity Only Developer.  It's really hard to find and super competitive to find developers who are going to jump on a concept and build it.  That's not going to be a successful outreach.

Go read the above posts and you'll hopefully reframe the question and do it much better the second time.

TechEmpower Benchmarks and the Microsoft ASP.NET Core 1.0 Performance Story

I’ve had lots of conversations with fellow CTOs about the TechEmpower Web Framework Benchmarks.  Some really appreciate the value that they bring to help them understand performance characteristics of different frameworks.  Depending on the Technical Performance Requirements for your system, this could be really valuable information that is part of your framework selection process.  However, I’ve also had fellow CTOs tell me that they don’t find the test credible or that they don’t understand how their favorite framework doesn’t perform better.   Frankly, those two statements are often correlated. But when Microsoft is talking about “huddling around the benchmark” and “only making a pull request when it’s an order of magnitude of Node.js” – I would say that the benchmarks are providing real value to the development community.

Let me step back and tell a bit more of the story here.

You may or may not be aware that Microsoft just announced the release of ASP.NET Core 1.0: 

Today we are excited to announce the release of ASP.NET Core 1.0! This new release is one of the most significant architectural updates we’ve done to ASP.NET.  As part of this release we are making ASP.NET leaner, more modular, cross-platform, and cloud optimized.  ASP.NET Core is now available, and you can start using it today by downloading it here.

There’s a lot to like about ASP.NET Core 1.0.  It is a viable contender for all sorts of development efforts.  One of the things that makes us even more excited is that Microsoft has focused on is Performance as a core attribute:

With a significant rewrite of the web framework, we addressed some performance issues and have set aggressive goals for the future.  We’re introducing the new Kestrel web server that runs within your IIS host or behind another host process.  Kestrel has been designed from the start to be the fastest .NET server available, and our engineers have recorded some benchmarks to prove it.  With the backdrop of the standard TechEmpower Benchmarks, the team used these same tests to validate the speed of Kestrel and have some impressive numbers to report.

Another announcement also touts the benchmarks:

We used industry benchmarks for web platforms on Linux as part of the release, including the TechEmpower Benchmarks. We’ve been sharing our findings as demonstrated in our own labs, starting several months ago.

How did Microsoft get to this kind of performance.  Scott Hunter, Director of Program Management on the App Plat team at Microsoft, tells a bit of the story on the DotNet Rocks Podcast (starting around 19:00). 

I got a rash of customers who said to me, “Hey, we went to this TechEmpower Benchmark site.  And we saw where .Net was and where other technologies are, why should we be using your stack?”
…
Damian said – “I’m going to build perf lab and take a look at this thing.”
…
In the team room, the team would be huddled around the benchmark saying, “We got another 10,000 or 50,000 or 70,000.”
…
would only make a pull request when it was an order of magnitude of Node.js.  If I can get 2 Nodes, then I’ll do a PR. 
…
It became this thing in the team room where people kept piling in, and it became important.  Then as we started putting the numbers out there, the response was crazy.  The pinnacle of the responses was … Satya [Microsoft’s CEO] got an e-mail from somebody in the Valley, which we ended up seeing at some point. The person was basically saying, “Hey, I just want to let you know that non-Microsoft and non-DotNet people down here are actually looking at the numbers that one of your teams is doing and we find them super-exciting. He said there’s chatter on Slack channels and stuff from people who not be even thinking or talking about us.”

The Damian mentions is Damian Edwards.  You can see a talk he does on Vimeo also telling a bit of this story.


I have to mention that early in the video Damian asks:

Who’s heard of TechEmpower – okay most people. 

Wow, really - who's that audience?

Damian takes us through how they looked at the Benchmarks and what led them to achieving some remarkable results posted on their intro page:

This is exactly the kind of thing that we were hoping at TechEmpower when we came up with the benchmarks.  The fact that Microsoft made it a focus and applied resource to produce such exceptional performance is commendable, and the result is a solution that is provides tremendous value to ourselves and the developer community more broadly. 

Great job Microsoft! 

At TechEmpower, we are very happy to have been part of your journey. 

What are the Technical Performance Requirements for your Startup?

By far the most popular post on this blog is 32 Questions Developers May Have Forgot to Ask a Startup Founder.  It was originally written in 2011 and has had amazing staying power.  While I’ve updated it a few times, it continues to get at important questions that startup founders need to be asking.  I find myself sending it to startup founders all the time – maybe just slightly less than Free Startup CTO Consulting.

One notable gap in the 32 Questions post is Performance.  Luckily, some of the folks at TechEmpower just posted Think about Performance Before Building a Web Application.  It does a good job of laying out different aspects of performance that should be thought about prior to creating a system.

I want to take a slightly different cut at the topic of performance.  While it’s a messy topic, I’m going to try to lay out some of the additional questions that developers should be asking a Startup Founder around the performance requirements of the application.

To get us started and to grossly oversimplify performance, conceptually we can think about the system as consisting of the following elements that I’ll refer to throughout the post.

• Requests.  We get a set of requests for our system to do something – generally from users or external systems.
• Compute.  Our system must access our data, possibly 3rd party services, do some calculation and then get back to the user or the other system with our response.
• Response. The pages or API response we provide back.

Application Characteristics

Any discussion of performance starts by understanding what the software does, how it is used, and what it interacts with.  A developer should find out:

• What are the different types of users?  What do they do?
• Is SEO important? – this is really another type of user – a crawler
• Are we providing an API to other systems?  What are the characteristics of how these are used?  - again, this is like a user type.
• Are there any time-based operations?  Overnight calculations?
• Are 3rd party services used?  What are the characteristics of how they are used?  What are their performance characteristics?
• How many of each type of user are there?  How many might be using the application at the same time (concurrent users)?  Will there be spikes of concurrent usage?
• What data is used in the application?  How big is the data set?  Are there complex aspects to the data?
• What computations / algorithms are part of the application?  Are any of the calculations done often?  Are any of the calculations complex?
• Are there any aspects that have specific performance needs?  For example, are you providing a stats service that needs frequent, fast updates?

Response Time

Once we understand the overall characteristics of the application, then we want to drill down on some specific performance characteristics.  We generally start with response time needs because, in many ways, this is ultimately the measure of performance.  If you think about our system picture above, response time is roughly the time it takes to get our page or API call back from the system. 

It’s well documented that response time has significant business impact:

• An ecommerce site that makes $100,000 per day could lose up to $2.5 million in sales every year for just a 1-second page delay.
• It’s also necessary to note that a poor mobile website experience can impact your customers’ perception of and loyalty to your brand.
• Google told us back in 2010 that site speed was important for SEO.
• 500ms increased response time means 20% less traffic for Google,
• 100ms increased response time decreases Amazon sales by 1%

The impact is quite real.  But as with most things in tech, the picture is far more complicated than that.  Consider two different types of systems:

• eCommerce or Content web site.  These will have many individual web pages, with specific URLs, optimized for SEO.  Each page needs fast response time (both time to first byte and total load time).  Pages may not have much dynamic content on the page. There may be lots of pages.
• Web Application such as Web Mail or a gated Social network.  The content is not used for SEO so response time characteristics may be quite different.  If the initial load time of the web application was 10 seconds but bringing up an individual email took less than 1s that’s likely an okay characteristic.  Technically, this may open the door to a single-page application (SPA).  These often often have a relatively longer time to load and then has really good performance once you are “in the application.”

Of course, response time is quite a bit more complex than this.  You will be looking at aspects like:

• Time to first byte (TTFB) vs. Load time
• API calls
• Global delivery?
• Mobile delivery possibly with slow connections?

As a startup founder, you need to think about the characteristics of your solution and what you need from a response time standpoint.

Request Volume

Assuming we know what our system needs to produce (the right side of the picture) and how fast (response time), then the next big question is really how much?  We want to find out what requests the application gets (left side of picture) and how often these come in.  This is generally turned into a Requests per Second number.

Most of the time we will start by asking about Concurrent Users – and this is generally the number that startup founders are thinking about when they talk about scalability.  Concurrent users are the number that are on your web site or web application at the same time.   Of course we need to combine number of concurrent users with what the users are doing in order to have more of a picture of what this means. 

For example, let’s assume this is a content site.  For human users, they request a page with content, likely the content page is relatively simple, the user reads/scans the page for a little bit, they decide to click something else which requests a new page.  This may take 10 seconds.  So some quick math:

• Each user generates 0.1 requests per second
• 1,000 concurrent users generate 100 requests per second

Those are really interesting numbers for a technical person.  Of course, this gets much more complicated.  A developer will want to drill down on:

• Different types of users?
• Different use cases?
• Traffic spikes?  TV Coverage?  Real-time events?
• API Usage?
• Growth rates?

This will give us a clearer picture of Request Volume for different kinds of requests that our system needs to process.

Complexity

Now we know the volume we need to satisfy coming in on the left and the response time required on the right.  The middle is what the system needs to do in order to respond to that volume of requests within that timeframe. 

Developers will want to explore with a startup founder where there may be complexity in the system.  We want to do this for two reasons: (1) how complex is the software we need to build – complexity generally means more time/cost to build, and (2) how long will it take for the system to calculate responses.  I’m only going to focus on the second aspect – understanding complexity as it relates to performance.  And really I’m only going to scratch the surface here as complexity is something that a startup founder and a Technical Advisor would need to explore together.

• Computation Complexity – What do we need to compute?  What are some of the more complex aspects of system calculation?  Natural language processing?  Matching algorithms?  Complex reports?  Are there widely varied use cases with different performance characteristics?  Any blocking operations?
• Data Complexity – What data are we dealing with? How big is the data set?  What are the largest number of a single type of entity?  Are there aspects that need to be pre-computed?  Any time series data?  Any logging/auditing data?
• 3rd Party System Complexity – What are the characteristics of the 3rd party systems?  What will happen when they are slow or non-responsive?  What happens when they return poor quality results? 

Last Thoughts

Yikes, that turned into a lot more than I was originally thinking as I started this post.  Hopefully the core model makes sense.  As a startup founder you need to think about the characteristics of your application and then think about the Volume, Complexity and Response Time requirements.  For some applications, it will be relatively straight forward to think about the technical performance requirements for your startup.  However, in many cases, this is a place where you really should be talking with a technical advisor or reaching out to get Free Startup CTO Consulting in order to understand what you need.

Los Angeles CTO / VP Engineering Job Searches

As the organizer of the LA CTO Forum, I get lots of inquiries by job seekers and people looking for CTO / VP Engineering talent. 

I’ve written quite a bit about aspects of this topic, especially from the perspective of startup founders looking for talent – you can find these in: Startup CTO.  This includes links to CTO Salary and Equity Trends, Technology Roles in Startups, Initial Conversation with a CTO or Technical Advisor, Finding a Technical Cofounder for Your Startup, Hiring a CTO for Your Startup and many others.

What I’ve not written as much about is what to do if you are a CTO looking for your next opportunity – especially in Los Angeles.  I have quite a few conversations like this and am having one via email right now, so it inspired me to put it in a post instead.

Targeting Your Job Search

The best starting place is to visit my post on: One Page Job Networking Tool.  It suggests that you start by creating a one pager that contains:

• Background - two sentences
• Job Sought - two sentences Company
• Characteristics - geography, size, industry, etc.
• Companies - a list of 25 companies that fit the bill.

This tool forces you to focus on the specifics of who you are really targeting.  When I get into a conversation with a CTO looking for their next role, they really need to know the stage of the company (pre-seed, seed, A, B, growth, pre-exit, public/on-going), size of the company – especially numbers of technical resources, geography, etc.  Ideally, they’ve thought through all of these characteristics.  It’s a good idea to start with a fairly narrow definition.

If you are going after venture-backed startups, then certainly look at socaltech.com and formds.  This will give you a pretty good initial list of companies that have raised capital in the geography.  Yes, this is going to take a while, but you need to spend the time to figure out who you are really targeting.  You should spend time looking at the bios and titles of the people in the company.  That is likely the best indicator of whether they might need a new senior technical leader.  Of course, just because a CTO or VPE is listed doesn’t mean it’s working well.

Armed with your networking tool, now it’s time to get it out to all the people you know.  You are looking both for introductions to the targets you know about, but even more importantly finding out who might have needs that you don’t know about.

What you should be gathering from this is that looking for a job is more of a sales process than anything else and there are no easy answers.  You need to start by figuring out who your suspects are.  How could you search and identify the companies that would hire you?  And then how do you move them through your pipeline?

Executive Recruiters

CTO job seekers often ask me for introductions to executive recruiters.  There are some really good executive recruiters here in Los Angeles that cover most of the CTO job searches especially for venture-backed startups.  Top of mind and in no particular order:

• Jim Jonassen
• Eric Larson
• Mark Landay
• Todd Gitlin

Note: if I’m missing someone, please let me know.

My experience has been that executive recruiters would really like to know you if you fit the profile of a current search.  Otherwise, they are not going to spend time with you.  If you think about it, that makes sense.  They are going to search out candidates when the time comes.

So, the bottom line these days is that I’m not doing these introductions.  If you have other thoughts on this topic, please comment.

 

VCs / Investors

Another common inquiry is, “Should I get introduced to VCs or other Investors who might need help in their portfolio companies?”  My general answer is “no.”  Much for the same reason as with executive recruiters.  The chance that you fit a specific need is relatively small.  Since they don’t know you already, it’s probably not worth their time or yours.

That said, if you already have a relationship with a VC, letting them know you are on the market is a good idea.  Actually, you should use your one-page networking document with them so they can likely help even outside their portfolio.

What Startup Advisors Do I Need?

Bob Dorf just published a post Where are the Hackers?  Solving the Founder-Tech Gap that came out of some fun conversations that Bob and I have been having.  A large part of this conversation is what kinds of advisors startups should be looking for.

A little while ago, I suggested that Every Web/Mobile Startup Should Have a Technical Advisor.  The conversation with Bob was about what the composition of advisors should look like.  We both felt that most startups are not taking a very systematic approach to defining with they need in terms of advisors.

Here’s the other aspect that both Tony and I preach: get help. You can’t afford and don’t want to hire a full-time CTO or architect. But, advisors, coaches, and mentors can often fill the bill. Getting someone who’s fully employed somewhere else to work with you on a limited basis to help close the gap is hugely important for the non-technical founder.

While Bob’s post focuses on Technology Advisors and the Startup Founder Developer Gap, we also discussed advisors more broadly.  I wanted to capture some of the broader conversation.

Formal vs. Informal Advisors

In many cases, you can get a couple coffee or beer meetings with advisors without ever formally engaging them as an advisor.  For me, if I can help you within a couple hours Free Startup CTO Consulting Sessions, I’m happy to do that and I don’t expect compensation or equity for that.  It’s not until it gets beyond the initial conversation or two that a formal relationship would be discussed.

There are a lot of people in the startup ecosystem that are happy to do this.  In creating Mentor Night, I’ve been happy to hear how giving most people are.  If you present a mentor with an interesting startup challenge in a space where they have experience or expertise, the mentors are quite willing to spend a few hours to help the founder.  And it’s way more fun when you have other interesting people in the room trying to also help.

Formal relationships make sense once you get beyond the informal stage, and it’s clear that there’s on-going need.  I recommend looking at the Founder’s Institute Founder Advisor Standard Template (FAST) Agreement as a template for this relationship.  Of course, you will want to work out the specifics of how you plan to work together with the advisor once it becomes more formal and adjust accordingly.

In some cases, Founders are building an Advisory Board with the purpose of padding their investor deck.  Investors discount this.  And it can hurt you if it’s purely cosmetic.  They may know some of your advisors and make a call after you meet with the investor.  

Connected Advisors?

I talk to many startup founders who select advisors in order to tap into their connections.  I’m not the biggest fan of this personally.  I side more with Mark Suster who says:

“advisory boards are an expensive equity proposition for merely introductions.”

Yes, you want connected individuals, but you often find that there are a few introductions that come easily and once those are exhausted, the value drops rather fast.

Domain Experts and Functional Advisors

Domain Experts have deep knowledge of your particular domain or aspect of the domain.  Maybe it’s knowledge of the players and dynamics of the mobile ad ecosystem. 

Functional Advisors come in with expertise in a particular area where you may need a second set of eyes.  This might be technology, marketing, sales, operations, international expansion, etc. 

Shafqat Islam looks at how he defined his Board of Advisors for NewsCred:

We spent a lot of time thinking about the exact roles and responsibilities for our advisory board. In that time I realized that we sought out very specific functions and had clear expectations.

Through this he defined aspects like “deep dives into our marketing strategy” and “product feedback and product strategy.”

This is a great way to go through and look at where you might have gaps and figure out what kinds of advisors you might want to approach for informal advice and then possibly formal advisory relationships.

In Bob’s post, he tells startup founders to get smart on product design, software architecture and development process.  That’s great advice.  But if the founder is just learning about these things, then those are gaps where getting advisors likely make sense.

Additional Thoughts on Advisors

Some additional random thoughts on Advisors and links to more information:

• Find advisors who say, “I don’t know but let me look for someone who does.” 
• Know how to navigate your Initial Conversation with a CTO or Technical Advisor
• Advisors 101 for Startups
• Everything You Wanted to Know About Startup Advisors Part 1
• Everything You Wanted to Know About Startup Advisors Part 2
• Five Things to Consider When Selecting Advisors for your Startup
• Why assemble an advisory board?
• Startups and Advisory Board Members
• The Importance of Advisory Boards for Startup CEOs 
• Critical Considerations for a Startup Advisory Board