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 45 people (half stateside, half abroad), and last year we did $2mm in revenue.
A little bit about our journey: every year in our short existence has been about continually striving for perfection. 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 technical leadership that has been with us for an average of 2+ years. But as our project load has grown in number and size, we've hit some scalability challenges. Everyone is working their butts off and more overstretched than ever.
Right now our goal is to innovate inwards. Continue striving for perfection, but within an empathetic and supportive environment where our team members can focus on becoming the best version of themselves. Instead of reacting to project needs, staff our personnel on fewer projects where they can focus and have room to be creative, and hire new personnel to meet demands proactively. We recognize that TopFlight can achieve natural, sustained growth only if our employees have room to grow alongside.
As our Director of Operations, you will lead us from A to B by stabilizing the rocketship. 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 are comfortable with being uncomfortable. Despite being a 45-person organization, we have a very fluid and dynamic culture. People oftentimes overstep their job titles to help solve problems.
- You are comfortable with radical transparency. If you don’t know what this refers to, read from Ray Dalio.
- The thought of engaging in constant 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.
- Grit & grind is how others might describe you. You aren’t expecting this to be an 8-5 job immediately, even if that is the eventual goal with systems fully in place. 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.
Our firm handles anywhere between 30 and 50 simultaneous projects of different scope. This means getting the right personnel (designers, product managers, technical project managers, developers, QA) into projects, while making sure those projects deliver on budget and timeline, while making sure that workers are happy and not at risk of burnout. This is an incredibly hard balance act. Resource planning is therefore your first big pain point to solve. Breaking that down further:
- Understanding staffing needs this week (across fixed price projects and retainers)
- Understanding staffing needs next week (across fixed price projects and retainers)
- Ensuring employees are not over- or under-worked
- Understanding delta between needs and haves
- Fuelling hiring pipeline by delta (1 month lookahead)
- Minimising developer churn (good people)
- Swapping staffing mid-project (typically, when developers need to be replaced)
In the longer term, other pain points to resolve are:
- Streamlining monitoring of project health so we can identify risks earlier (we currently do a lot of fire-fighting)
- Aligning product team and sales to prevent overpromising
- Managing key client accounts and negotiating additional LTV (example: converting a fixed price project that’s ended into an ongoing retainer, or converting an ad hoc project into an ongoing retainer)
- Improving our project outcomes by improving efficiency and innovation
- Running interpersonal interviews for new hires (technical and non-technical)
- Setting focused OKRs that simplify how we measure the company’s overall performance and productivity on a daily basis
- Making sure our evergreen Standard Operating Processes remain up to date
Again, this position is going to a big challenge for just about anyone. We’ll work our butts off and struggle intensely to solve big problems, but potentially see tremendous growth and improve many people’s lives. If this is a challenge that excites you, we can’t wait to hear from you.Apply for this Job