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 to solve them your way and the trust to do it without a manager in your inbox.

Work that ships and matters. What you build reaches real consumer brands fast.

A category we are creating. The Agent of Record is new ground, with unsolved problems and cutting-edge models, not a crowded field to compete in.

A team that respects your judgment. Globally distributed, async-first, low bureaucracy. We hire adults and treat you like one.

Great salary plus equity or stock grants. Own a piece of what you build.

Learning budget. If you are growing, so are we.

AI-fluency by default. Few places will push your work with production AI further or faster.

Our values

The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedback - both giving and receiving it - because they care more about getting things right than being polite.

They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that's how great work gets done. When things get tough, they adapt and keep pushing forward.

Our approach to AI

The people who thrive here treat AI like a natural extension of themselves. They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code. They know which AI works best for what problem.

Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. But the magic happens in how we share knowledge. Demo days where someone shows off a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows.

At Siena, we're not just looking for people who can do a job. We're looking for people who want to break boundaries, create the future, and reshape industries. If that's you, we look forward to your application.

How we hire

We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at [email protected].

Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.