Startup CTO Coaching

My name is Chris Simon and I help startups turn their vision into reality by working with their CTOs.

I was a startup CTO for most of my career: I was the technical co-founder of InLoop, the business that brought Australian Fintech success stories Flexischools and LanternPay (Recently acquired by NAB) to market.

I’m also available to provide technology advisory services to boards, executives and engineering teams, but coaching startup CTOs is my primary activity.

CTO Coaching

As a CTO Coach I tend to work with first time CTOs who have a background in software development - perhaps as a senior developer, tech lead or engineering manager. I work with everyone from solo hands-on CTOs up to CTOs looking after teams of engineers in a startup/scale-up context.

A typical structure involves fortnightly catchups of 2hrs. We work together to set and work towards personal and team goals and balance that with tackling urgent issues of the day.

If you’re a new CTO, or a founder/CEO wanting to support your CTO, let’s have a chat about how I can help.

A development roadmap for startup CTOs typically follows the growth journey of the company:

1. Solo/Small Team

In this phase a startup CTO has a lot to do! The team is small and the CTO needs to be a hands on technologist but particularly if there are investors, there is a lot more to consider.

After reviewing gaps and challenges, we’ll focus on topics such as:

  • Developing an Entrepreneurial Mindset
    • Product-oriented Engineering
    • Contributing to business success as an Innovator
    • Risk Awareness, being intentional about Risk Appetite
    • Demand Management/Prioritisation & MVP Design
  • Technical Skills
    • Continuous Delivery / Value Stream Analysis
    • Architecture - Strategic use of Monoliths and Microservices
    • Quality Management
    • Cloud Architecture - Infrastructure as Code, Serverless
  • Business Leadership
    • Understanding Financial Positions (P&L, Balance Sheet, Fundraising Activities)
    • Being part of an Executive Team
    • Board Reporting as a CTO
  • Security
    • Preparing for future Security/Compliance Requirements
    • Right-sizing Security Effort/Response

2. Growing a Team

In this phase, the engineering function is growing and might be anywhere from 5-10 engineers.

Assuming the foundations from the previous phase are taken care of, the startup CTO needs to lean into people leadership and we’ll start exploring topics such as:

  • Engineering Talent Acquisition
  • Onboarding & Training
  • Building a team of Complementary Strengths
  • Psychological Safety
  • Establishing a Feedback Culture
  • Managing Energy not Time - it’s a marathon not a sprint
  • Establishing Engineering Processes & Reporting

3. Multi-team Engineering Department

Once the engineering headcount exceeds 10 it can become unwieldy to continue to operate like the small team you once were. You need to split teams which introduces a whole new world of socio-technical engineering. By this time it’s also typical that the rest of the organisation has grown and there may be dedicated folks handling functions such as People & Culture, Finance, Growth & Product.

Topics that we look at in this stage often include:

  • Organisational Situational Awareness
  • Stakeholder Management
  • Talent Acquisition / Brand Positioning
  • Organisational Design & Impact on Architecture
  • Scaling up Processes & Tooling
  • Maintaining a High Pace of Team Flow

Get In Touch

If you’re anywhere on the journey, from day 1 to your 30th hire, and would value an experienced coach to help you be the best CTO you can, get in touch and let’s have a chat!