Meet Siena
Siena is the Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns.
It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on.
The team
We are a small, fully distributed, global team. We have built leverage into how we work, which is what lets a team this size move at the speed we do.
We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on. Low ego, high standards, fast clock.
If you want to set the bar rather than follow one, keep reading.
The Role
Our current Engineering Manager holds the full picture across Channels, Analytics, Agents, and Integrations, and that context is bottlenecked in one person. We're scaling fast (Order Protection, Social Agent, Voice, and Shopping Agent are all spinning up in parallel), and the team is distributed across timezones our Engineering Manager can't fully reach.
This role closes that gap: you own engineering execution day to day, roughly 30% of what our Engineering Manager currently holds, so they can focus on strategy, customers, fundraising, and what's next. It's not a coordinator role. You run 1:1s, keep cycle cadence honest, write technical debt plans alongside engineers, and unblock people before problems become escalations. Scope changes and anything that reshapes the team are joint calls; everything else is yours.
What You'll Do
Delivery (~50%): Own the weekly cadence for Channels and Analytics, surface and sequence priorities with PMs and engineering leadership, unblock engineers proactively, and write technical debt plans with engineers, not for them
Developer Experience (~25%): Improve the things that slow good engineers down, bring structure where it adds speed, and resist adding process for its own sake
People Development (~25%): Run 1:1s that leave engineers with clearer thinking, deliver hard feedback directly, help senior engineers grow toward management, and act as a backup hiring partner
Who You Are
The Bar: If you're missing any of these, this isn't the role for you.
3+ years managing a team of engineers in a product-delivery capacity: you've owned outcomes, not just people
Startup or scale-up experience: you know what it feels like when there's no process and no safety net, you've built from 0-1
Genuine AI/LLM fluency: you understand agentic systems, evals, and model reliability, not just that "AI is changing everything"
Strong Signal: Not dealbreakers, but what separates a good hire from a great one.
Technical credibility: not the best engineer in the room, but credible enough that senior engineers route hard problems to you, not around you
Experience with security, compliance, or SOC-adjacent work
Worked without a dedicated TPM or staff engineer as a crutch
Experience managing senior engineers who need a thought partner, not a process owner
Not a Fit If
You're in a fully hands-of managerial role
You need a fully defined process to operate
You want to redesign the org or introduce career ladders before shipping anything
Your primary achievement track is headcount growth or reporting lines rather than what actually shipped
Why Siena?
Real ownership. You will own problems, not tasks, with the autonomy t
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