Have you spoken with a Chief Technology Office before? Are you one yourself? How do you know if you are doing an objectively good job? When I first started, I used intuition with my limited exposure of the world around me. I feel productive, I feel the needle moving based on my doing. But this productivity matrix is too context-dependent. What may be good in your current company may not set you up to be a good CTO in other companies.

The purpose of this article is find out what is your yardstick of a 90% percentile performance and what is a 10% percentile performance based on the context of your company’s stage.

What is good of a CTO in an early stage startup may not be good for a CTO in a growth stage startup.

I’ve previously written what does a CTO do across the growth stages here. It is about time to revisit that article.

Mission of CTO

• Someone you can trust with long-term technical strategy

Take the rein on company’s technical direction
Find balance between technology and business through budgeting, networking and researching
stay on top of technology as a whole, being responsible for keeping the company’s technology as up to date as possible

• A person of the people

Your CTO should be exciting and inspiring every member so they can do the best work. You are incharge of the culture that are talent attractive. You want a team that collaborates.

What is not a CTO?

1. The best developer in the company

The goal is for CTOs to hire strong engineers whom juniors can reach out for technical questions.

2. The Technical Architect

CTOs do not have to make all the technical decisions. Instead, they should be the one to create processes to allow personnels to make sound decisions with right guidelines.

3. The businessman who does not understand technology or the engineer that does not understand business

Time Allocation

A) External - 70%

• Reaching out to make sales, liaising with customers (35%)
  • Understand the needs of customers including any issues that arrive with the sales process, the product iteself, or something else within the company.
  • Consistently figuring out how to close customer accounts
  • Comfortable with product demo
• Business development & partnership(15%)
  • Being an ambassador including at technical associations
• Marketing and analytics (20%)

Knowing how to outreach and network is a big part of CTO that cannot be delegated. That said, CTO should also follow similar companies to stay on top of competition.

A framework to assess your approach to a problem: NABC

• Needs
• Approach
• Benefit per cost
• Competition

Knowing how to assess your competition is an important component of winning in the market.

B) Internal - 30%

• Team management
• Business planning
• Technological Directing
  • Typically serves as the solution architect

Generally, I like the analogy of Ray Dalio Everything is a Machine.

Whatever you do in your internal process, think of them as a machine. You have a desired output, productivity. You need inputs: engineers, product designers, client feedback. Through that input, it goes through a series of rollers, gears and processes to deliver to you a freshly baked productive result.

Whenever you do not get the desired output, then explore the parts in the machine that requires refinement or changes. Find out what additional inputs you may require to produce that output you desire.

I like this concept given its deterministic nature. If you want an output, there are structured repeatable ways to achieve them. You do not have to wish or hope for desired outcomes. This mental model helps to put more control back into your hands.

How to measure CTO performance?

1. Tech Strategy Alignment

• Every time a company misses a key tech trend, its on the CTO
• Misalignment between technology and business strategy, its on the CTO
• How well the tech strategy lines up with the business strategy. Trechnical strategy should be an effective support to the overall business model.

2. Health of engineering culture

• Speaking to individual members of the team
• Find out if they are happy w the culture. If happiness index is high, its a good work done.
• CTO is expected to help recruit and retain top talent. Innovative, work friendly environment has to be done
• Engineers need vision to piece together their every-day work so they can understand how their nuts and bolts is supporting the ship
• VP of engineering should be satisfied - not annoyed - with the CTO’s contribution.
• Having a high-performance/ high-grace culture will be crucial. Learning how to improve the team’s performance will be a dependency you need to have. You can check it out here

3. Internal CSAT

• A way to measure internal satisfaction
• Going to CTO for advice on resolving tech-related issues, and initiatives.

4. Team Engagement

You want to understand how engaged are your talents. Often times the technical team is the most expensive in a technology company, you want to make sure these people are aligned with top management.

5. Cash/Time Ratio

CTOs are typically digital transformation executives. You want to know how to (1) do digital transformation, (2) assess your strategies for digital transformation within the company’s constraints.

6. Tangible value for your business users

Please avoid the ‘shiny object syndrome’. Number 1 focus is to create value for your end users - value that can be tracked, reported on, and replicated.

How much cash is it going to take (including headcount and resources), and over what period of time will that cash be deployed to hit our outcome?

Reference

CTO Performance Metrics

1. Team Attrition Rate
   Number of people leaving the company. If company’s attrition is low, its probably better business with better management

2. Uptime/ Downtime rate

3. Team Velocity

4. New bugs over time
   The lower, the better

5. New critical bugs over time
   A high number is a red flag

Reference: Performance metric

CTO Job Description across Startup stages

Responsibilities & Requirements of CTO

1. Business idea

Works with engineering team to ensure the most reliable development practices to develop core product.

Responsibilities

• design core product
• Rapidly iterate and test first MVP
• Make Architecture decisions to ensure a strong, stable, and scalable product
• Building tech stack and engineering hiring plan
• Work with engineering team to increase expertise and understanding of best practices

Requirements

• Experience with early-stage successful tech start-up
• Strong product sense, and can build engaging tech for customers
• Ability to conduct technological analyses and research
• Strong interpersonal skills to share/collaborate with peers

2. Early Stage

Description

Startup has its MVP, few early customers along with their feedback, the CTO can make further arrangements to improve their product based on customer’s review

CTO becomes a stronger customer advocate with management duties to keep everything on track. Continuous improvement on the product along with technical development team.

Responsibilities

• Partner with CEO to define, prioriize and realize product roadmap
• Manage in-house engineering team, contracted development partners, and head the integration of partner APIs to our platform
• Driving performance, efficiency and effectiveness of engineering/product team
• Discover & implement new technologies that yield competitive advantage

Requirements

• Significant experience in software architecture and personally building digital products from early-stage through scaling
• Managed, mentored, inspired small team of engineers providing architectural guidance, code review.
• Deep knowledge of full-stack modern development practices (example: DevOps, API integrations)
• Experience in project management to ensure timely deliverables.

3. Reaching product-market fit / consolidation
   More management, and decision making duties. Has multiple development teams that work on enhancement of the product under his command. Continuously tracks progress while paying attention to the arising security issues.

Security issues arising at this phase
You may consider having a Head of engineering to be active in designing product architecture while looking for new strategies popping up in the industry

Responsibilities

• defining product vision and strategy
• Aligning and providing feedback on the product roadmap, work closely with product to decide on prioritization, resource allocation, and timelines.
• Leading all aspects of development lifecycle, including requirements analysis, strategic planning, design/architecture, execution, deployment, and maintenance
• Building quality assurance and data protection processes, ensuring all technology practices adhere to regulatory standards

Requirements

• Prior CTO / Head of Engineering / Technical Visionary experience for early stage startup, preferably with track record of one or more successful exits
• Data-driven to evaluate product-market fit and other aspects of product performance, able to identify insights that will influence future decisions
• Have proven understanding of best engineering practices for full software development life cycle (SDLC), including coding standards, code review, source control, build, test, deploy, and operations
• Effective leader and team-player - knows how to hire and manage the right talent to scale the engineering team

4. Growth

• Growth stage have strong emphasis on collaboration with many companies
• need framework to balance technical resource usage - to ensure all resources are efficiently and securely used
  • using his soft skills to keep development and engineering teams motivated
• Strong leadership skill is required in this stage

Responsibilities

• Communicate technology strategy to partners and investors
• Ensure technologies are used efficiently, profitably, and securely.
• Develop strategy and framework for allocating resources effectively in line with vision - motivates and inspires team members
• Setting goals that help meet organisation needs, set a high standard for success and draw on team managers’ strengths
• Building a technology leadership team that can expertly manage their own teams, develop a strong and focused culture, be responsive to the organisation’s needs.

Requirements

• 10+ years experience leading and being successful in tech industry
• Strong leadership, team building mgmt skills, track record of coaching and mentorship
• Strong communication skills to present technology vision confidently that motivates internal and external stakeholders
• Understands budget and business planning
• Strategic thinker

Reference

What is required of a CTO checklist

Reference: Qualities of CTO

1. Understand new & upcoming technology and trends,
2. Great network - have a strong network of developers
3. Product experience - customer focused
4. Communication skills (technical & non-technical) - transiting biz goals into technical goals
5. Deadline management - processes to improve efficiency. Realistic but effective
6. People skills

References

• Mission of a CTO
• Forbes Measure of CTO
• Measure CTO performance