Job Opening: CTO

Full-time. Remote or Boston.


We're looking for a new CTO to lead our small but mighty engineering team.

Our ideal candidate is technically brilliant, has experience leading teams of engineers, and is excited to contribute at a variety of abstraction levels (from nitty technical decisions to multi-year product strategy).

This position is open because after five years of excellent work, our founding CTO Spencer has decided to step down from his leadership role to become a part-time individual contributor.

Who we are

We founded Tuple five years ago because we believed a purpose-built pair programming tool would outperform generic solutions like Zoom or Google Meet. We were right, and the company has grown to millions in revenue and tens of thousands of paid users.

Today, we are a team of 10 with 6 engineers. Our engineering team skews very senior and self-motivated.

Our company culture is ambitious but calm, with great work/life balance: we work reasonable schedules (30-40 hours per week) and take plenty of vacation. The company is fully owned by its three founders, so there is no outside pressure to grow at all costs. Instead, we can hire slowly and focus on shipping an amazing product. This approach has worked well, and revenue is up ~70% year-over-year.

Tech stack

As Tuple is a persistently-connected desktop application for real-time communication, our stack is a bit atypical. Much of this stems from our choice to optimize for low latency and first-class integration with the host operating system above most other concerns.

Real-time communication is handled by a cross-platform engine written in C++. We offer native clients for Mac and Linux that wrap this engine. These clients rely on the engine for heavy lifting while integrating with OS-level APIs. The Mac client is mostly Swift and Objective C, and the Linux client C++.

Billing, user management, and other supporting features are provided by a Rails backend. Persistent connections and call negotiation are handled by a service written in Go.

Role overview

We believe a CTO has three primary responsibilities:

  1. Manage the engineering team.
  2. Ensure technical excellence.
  3. Act as engineering's conduit to the rest of the company.

Team management

Today, we have an engineering team of 6, and we'll expect you to manage those folks. We're big believers in the power of employee retention, and we'll want you to invest substantial effort into ensuring folks stay at Tuple a long time.

Your team is likely to expand over time, but not particularly fast. We prefer to hire slowly, let folks get fully integrated, and not hire again until we have a specific pain or highly-promising opportunity we can't pass up. Your team will double in size, but that would happen over the course of a few years.

When we do hire, you will lead that process. You'll get the final say over which candidates we hire, so you should be excellent at screening and interviewing. If someone isn't working out, you'll be responsible for leading that process as well.

Hiring, managing, and firing are hugely important levers, and we'll need you to pull them well.

Ensure technical excellence

Technical excellence means our product is high quality, reliable, secure, and constantly improving.

We have a wonderful Architect (hi Mikey!) for you to lean on, but you will be accountable for all technical decisions at Tuple.

This could be as small as a single-line change in a pull request, or as large as what language we use to write our (hypothetical) future Windows client.

With this authority comes responsibility. Bugs, downtime, reliability issues, and security problems all fall under your umbrella. You will need to monitor these areas, proactively look for issues, decide which ones need fixing now, and lead efforts to improve them.

(Good news: this isn't a rescue mission! Our average call quality rating is a 4.5 out of 5. We have excellent uptime and the app rarely crashes. We work with Latacora to regularly improve our security posture. Overall, the engineering org is performing well, and you get to make it even better.)

Importantly, you'll always remember that the point of all this technical excellence is to make a product our customers can love and rely on. That idea should energize you more than generic engineering prowess.

Act as engineering's conduit to the rest of the company

As CTO, you are the human API between engineering and the rest of the company.

For example…

  • When our CEO Ben is creating our product roadmap, you will work with him to ensure it is well-sequenced, tightly-scoped, and manages trade-offs well. You'll advocate for a good balance of bug fixes, refactoring, and new development. You'll help set reasonable deadlines and decide between cutting scope or letting them slip when needed.
  • When our Head of Success reports a hot issue affecting a customer, you'll make the tricky decision of which engineer to interrupt to go investigate.
  • When the leadership team (CEO, COO, and you) meets (quarterly, in person) to make difficult decisions around hiring and product strategy, you'll weigh in thoughtfully, balancing engineering's interests with those of our users and the rest of the company.

A note on our outgoing CTO

This position is available because our current CTO Spencer has decided he’d prefer to be a part-time individual contributor at Tuple. This transition is happening amicably, and Spencer is excited to hand off his CTO duties to someone who can take our engineering organization to the next level.

As an owner, Spencer will occasionally provide high-level guidance to the executive team as part of our “board”, but will be fully giving up his day-to-day leadership responsibilities.


  • Experience leading and managing a team of developers
  • Deep technical wisdom honed over years
  • Excellent soft skills (empathy, confidence, conflict resolution)
  • Strong communication and writing skills
  • An interest in the things that make Tuple unique (pair programming, native apps, real-time communication)


  • Proximity to Boston or a willingness to relocate so you can work in person with our CEO, Ben. (Yes, we are aware of the irony.)
  • Experience with RTC or desktop apps

How to apply

Please demonstrate your excellent writing skills by writing a tightly-edited pitch for yourself. When you're done, email it to