Topflight is a product design and development company that conceptualizes and delivers software for fintech, healthcare, and other high-impact industries. I started the company in 2017. Today we have a team of 50 people (40% stateside 60% abroad). We’ve bootstrapped our way to 50% annual growth, and this year we’ve done $2mm revenue to date.
A little bit about our journey: every year in our short existence has been about continually striving to become the best at what we do. We spent years hustling to deliver on client outcomes by getting the right people on board. To a large extent, we have. We now have an extremely hard-working and motivated group with a “sink together, swim together” mentality, steered by leadership that has been with us for an average of more than 2 years. Our work has helped our clients raise over $165 million to date, ranging from venture-backed startups like Dermasensor to Fortune 500 companies.
As we look forward to the next 2 years of growth, the theme is Structural Improvements for us to scale and make sure we continue delivering great products on time, on budget, without sacrificing technical debt, while still adapting to evolving markets. To that end, we’re seeking a fearless new Chief Technology Officer.
We recognize that TopFlight can achieve natural, sustained growth only if we hire the best people possible and also give them room to grow alongside us. As our CTO, you will be in charge of hiring, empowering, evaluating, and also removing underperformers. This is going to be a very hard position where the challenge varies by the week if not day. It's very much an early-stage startup environment, with some chaos and a high risk-reward ratio where your execution can make visible impact immediately, and seriously impact lives inside and outside of our organization for the better for many years to come. Below is what we’re looking for in a candidate. We’ll start with the “Who” before diving into the “What”, as we’ve learned that Who is far more important in finding the right fit for this role.
- You still love writing code.
- You’re passionate about learning and applying the latest technologies.
- You’re considered a mentor by other developers.
- You are comfortable with being uncomfortable. Despite being a 50-person organization, we have a very fluid and dynamic culture. People oftentimes overstep their job titles to help solve problems.
- You have a knack for consulting others on how to best achieve a feature for scalability and their business goals (as opposed to waiting for instructions on how to build a feature, or building something the first way that comes to mind)
- You have the ability to "figure it out" when you hit inevitable roadblocks.
- You have a desire for constant learning and a dynamic change-up in project opportunities.
- You don’t think you’re above strict accountability for deadlines, matched with proactive discussion of deadline adjustments.
- You have the mental fortitude to handle tight deadlines and rapid development cycles.
- You are comfortable with radical transparency. If you don’t know what this refers to, read from Ray Dalio.
- The thought of engaging in rigorous debate to identify the facts of any situation does not scare you. You are willing to have difficult and lengthy written as well as verbal conversations to gather facts from multiple stakeholders, before finally suggesting a solution. This comes from “Good to Great” by Jim Collins.
- Once you have a solution in mind, you lead by doing. If you have an idea to improve operations, you tend to start by experimenting and iterating with your own implementation of it to the point where it works elegantly and without error, before passing off a working model to others on the team to rinse & repeat.
- You aren’t expecting this to be an 8-5 job. You do what it takes to get things done, and there will be times when you need to be more available than others.
- You’re able to get buy-in from different backgrounds and different departments, each with strong opinions. You never rely on authority or job title to drive compliance. Persuading intelligent and thoughtful teammates by helping them understand why they should do something is your strong suit.
- You resonate with the rest of our Culture Statement.
- Mentoring and empowering developers into the best versions of themselves.
- Balancing the needs of 20 different projects instead of 1, which is a key difference from working for a single-product company.
- Architecting the optimal approach for developers to execute on.
- Reviewing code quality for each sprint.
- Conducting developers weekly performance reviews during their 1st month trial, then monthly thereafter.
- Analyzing developers’ work relative to their estimates and also providing “smell tests” on new estimates.
- Hiring elite developers for communication, teamwork, problem-solving, and of course coding proficiency.
- Working with leadership and HR to minimize developer burnout and create a positive culture for developers.
- Pushing adoption of new languages and APIs by considering efficiencies gained (lower dev time for same result), hireability, and new markets they would allow us to tap into.
- Working with devops to ensure compliance (HIPAA, SOC2, GDPR) and best devops practices.
- Working with our QA Lead to optimize dev-to-QA cycles.
- 100% remote, WFH opportunity.
- Work-life balance. We try to get things done efficiently, then enjoy the rest of our lives, especially on weekends.
- $120k base salary, negotiable based on experience and fit.
- Healthcare insurance reimbursement.
- Guideline 401k with 50% matching contributions (for w2 employees only).
- Performance-based bonus or profit-sharing. KPIs for either program would be mutually agreed-upon.
- Complimentary wealth management mentorship.
- Flexible vacation and sick days, with 7 days of PTO per year.
- $1,000 new equipment stipend.
If this sounds like an exciting and suitable challenge for you, please add to the top of the cover letter your answer to this question: "Your developer goes over their own estimates by 50%. What do you do?”