Twenty Staff / Principal Technical Program Manager at Twenty manages product and engineering planning cycles to ensure delivery commitments are met. This role maintains honest plans and escalates risks early to leadership.
Responsibilities
Our software ships to government customers, and much of our roadmap is tied to deployment milestones that customers and missions depend on. Working with our deployment managers, you'll keep a register of those commitments, link each one to the roadmap work it needs, and make sure that when priorities change, the tradeoff against a commitment is made explicitly and on the record by the people who own it. Done well, this means customers and missions can count on what we've promised them, because any change to a commitment is a decision the right people made together.
You'll report to the VP of Engineering and work alongside your peers, Twenty's product managers, engineering managers, and deployment managers. The role is neutral: you hold everyone to the commitments they make, from individual teams to executive leadership. When plans and results start to diverge, you raise it early and work it through with them. When a problem needs a decision above the teams, you have the standing to take it directly to the VP of Engineering or the VP of Product. At Twenty, ideas are easy and execution is everything. This role keeps our pace aggressive and predictable at the same time.
Run the planning cycle from intake through close-out. Lead planning sessions with PMs and EMs, and make sure requirements are clear enough to break down and design against before a team commits to the work.
Hold teams to the planning process. When a step gets skipped, work with the PM and EM to get it back on track, and bring it to the VPs only when the teams can't resolve it themselves.
Maintain the sizing standard, question estimates that don't hold up, and track estimates against actual effort so that they improve over time.
Own the rolling delivery forecast, with dates and confidence levels.
Run the status cadence across all active work, and produce the program-level rollup for executive leadership.
With the deployment managers, maintain the register of deployment milestones, link each one to the roadmap work it depends on, and review milestone health with them regularly.
When a roadmap change affects a milestone, make sure the PM, the deployment manager, and the right VP make the tradeoff explicitly.
Maintain the map of dependencies between teams and the program risk register.
Run end-of-cycle retros on how well plans matched results, and improve the planning process from what they show.
Qualification
You hold productYou write for two audiencesYou're motivated by mission workYou've held people at every level
Required
You keep plans honest without turning planning into bureaucracy. Teams leave your sessions with a clearer plan and less overhead.
You say a date is at risk while there is still time to do something about it, and you say it in plain terms.
PMs and EMs trust you because you help fix the problems you find.
You hold product, engineering, and leadership to the same standard, and people on every side trust your read of the plan.
You use data on estimates and outcomes to make planning better each cycle, and you share it in a way that helps teams improve.
You write for two audiences: engineers who need the detail and executives who need the decision.
You're motivated by mission work, where a missed date affects a customer's operation.
You can read a product requirements document and judge whether it's ready for engineering to break down and design against. When it isn't, you can say what's missing.
You learn a product and its customers' domain in enough depth to understand what each piece of work is for and whether or not its requirements, design, and estimate fit together.
You've run a recurring planning cycle for multiple teams, from intake through commitment and close-out, and you can describe what you changed when it wasn't working.
You've owned a delivery forecast or set of committed dates that leadership relied on, and you can show how you measured and improved its accuracy.
You've held people at every level, executives included, to the commitments they made, and kept their trust while doing it.
