Principal Software Engineer
•Skimmer· 2d
💻 Engineering⏰ Full-time🎯 Lead / Principal🇺🇸 USA
2d ago
Siena·2 months ago
Siena is the Agent of Record for consumer brands. One agent that owns the entire customer journey, running on a shared intelligence layer no point tool can replicate.
Consumer brands run ten or more disconnected tools to manage their customers. We collapse that stack into a single agent. It started with support, the hardest surface a brand has, and it expands from there: Shopping Agent, Social Agent, Siena working alongside a brand's own operators. One agent across every surface, with shared memory, shared context, and shared tools.
Hundreds of brands already run real customer volume on Siena in production. This is built, working, and growing, and we are racing to build what comes next.
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 own real problems rather than close tickets, keep reading.
About the role
Our current Engineering Manager holds the full picture across Channels, Analytics, Agents, and Integrations. That context is bottlenecked in one person - and that's a problem we're close to feeling. We're scaling fast: Order Protection, Social Agent, Voice, and Shopping Agent are all spinning up in parallel. The team is distributed remotely across different timezones, making working hours and proper oversight hard to properly meet.
This role exists to close that gap. We need someone who owns engineering execution day-to-day - taking roughly 30% of what our Engineering Manager currently holds - so they can focus on strategy, customers, fundraising, and what's next.
This isn't a coordinator role. You run 1:1s, keep cycle cadence honest, write technical debt plans alongside engineers, unblock people before it becomes an escalation, and act as a genuine thought partner on the operational side. Scope changes and anything that reshapes the team are joint calls. Everything else is yours.
What you'll do
Delivery (≈50% of your time): Own the weekly cadence for Channels and Analytics. Our Engineering Leadership is out of the loop on day-to-day - but always knows what's happening. Work with PMs and engineering leadership to surface and sequence priorities - including the ones nobody has written down yet. Help organise backlogs and bring structure to teams operating in a fast-moving, low-process environment. Unblock engineers proactively. Identify the constraint before it becomes an escalation. Write and maintain technical debt plans with engineers, not for them. Act as a second thinker on integration strategy and capacity planning.
Developer experience (≈25%): Improve the things that slow good engineers down. You don't need permission to start. 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, not just status logged. Deliver hard feedback directly. Have it land, not bruise. Help develop senior engineers who want to grow - including coaching engineers who have ambitions toward management. Act as a backup hiring partner: help run loops, hold the bar, partner with recruiting.
What you'll bring
3+ years managing engineers in a product-delivery capacity — you've owned outcomes, not just people
Based in a European timezone (UTC to UTC+3) — this role exists specifically to be close to engineers our Engineering Manager can't reach from their timezone
Startup or scale-up experience: you know what it feels like when there's no process and no safety net
Technical credibility - not the best engineer in the room, but credible enough that senior engineers route hard problems to you, not around you
Genuine AI/LLM fluency: you understand agentic systems, evals, and model reliability -` not just that "AI is changing everything"
Experience with security, compliance, or SOC-adjacent work
Worked in a product company without a dedicated TPM or staff engineer as a crutch
Experience managing senior engineers who don't need managing in the traditional sense - they need a thought partner, not a process owner
What we're not looking for
Someone who needs a fully defined process to operate
Someone who comes in wanting to redesign the org or introduce career ladders before shipping anything
Someone whose answer to "what did your team ship?" is "that was a PM call"
Someone whose primary achievement track is headcount growth, org structures, or reporting lines
Someone pitching a VP trajectory or dotted-line authority on day one
What success looks like
Day 30: You've run two 1:1 cycles with each engineer on the team. You own the Channels and Analytics weekly cadence - our engineering leadership is out of the loop, but understands what's happening. You've read the last quarter of Linear, mapped the codebase shape, and met every integration owner..
Day 60: One concrete unblock in Channels that wouldn't have happened without you owning the planning side - even if that means surfacing refactoring potential. The security compliance work (Sprinto) is no longer single-threaded through one person: documented, distributed, or sequenced behind a milestone date. You've been to a customer meeting or shadowed the deployment team on issues to be tackled.
Day 90: A measurable delivery attributes to your planning, not your coding. Engineers proactively bring you problems they used to escalate upward - and team channels have broader engineering discussions, not just siloed problems. That's the trust signal. Our current Engineering Manager has recovered roughly one full day a week of management overhead. You work as a unit: they handle strategy, customers, and exec conversations; you handle execution, 1:1s, planning, and day-to-day unblocking. Hiring, scope changes, and anything that reshapes the team are joint calls.
Failure looks like: status reports flowing through you with no judgment added; engineers being polite but routing around you; our current Engineering Manager still running teams in practice while you sit elsewhere.
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.
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.
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.
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.