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

This role is not for most people, and that's the point. Our Enterprise customers are ecommerce and consumer brands doing $100M+ in annual GMV, and this seat is for someone who has already closed deals at that level. This is a hunter seat: you'll build your own pipeline and take six-figure, multi-stakeholder deals from first call to signature, with real RFPs and real competitive pressure. It's not built for junior reps: the deals are complex and the bar is high from day one. We want someone with a proven enterprise record who wants to do it again, at a company small enough that every win is visible.

What You'll Do

- Build and own your enterprise pipeline into ecommerce and consumer brands doing $100M+ in annual GMV.

- Run the full enterprise sales cycle from first conversation to close: multi-stakeholder, multi-SKU deals with cycles that can run six months.

- Lead formal RFP processes,



coordinating solutions engineering and leadership through each stage.

- Run executive conversations with CFOs, CX leaders, and full buying committees, tailoring the case to each stakeholder.

- Build the business case with real numbers, and defend it with finance and executive teams.

- Find and close expansion opportunities inside your own accounts.

- Know the competitive landscape and how Siena wins in it, deal by deal.

Who You Are

The Bar: If you're missing any of these, this isn't the role for you.

- Experience selling to executive and C-suite stakeholders at ecommerce and consumer brands.

- A track record of closing accounts doing $100M+ in annual GMV, with named brands and named numbers. Not "exposure to." Closed.

- Quota attainment or overachievement in the last 1-2 years that you can explain, not just report. "I exceeded quota" tells us nothing. We want to know why you won when others on your team didn't.

- Hands-on experience running formal RFP processes in six-figure, multi-stakeholder deals.

Robust Signal: Not dealbreakers, but what separates a good hire from a excellent one.

- Experience selling AI products, or selling into teams adopting AI.

- Quota overachievement sustained across multiple years, not one standout year.

- A track record of sourcing a meaningful share of your own closed pipeline.

Nice to Have: Bonus, not required.

- Experience selling usage-based pricing, with land-and-expand growth inside accounts you owned.

Not a Fit If:

- Your experience is mainly mid-market or SMB, with deal sizes well below six figures.

- Your closed deals mostly came from inbound leads, not pipeline you created.

- Your enterprise experience is mostly supporting deals rather than owning and closing

#J-18808-Ljbffr

📌 Enterprise Account Executive (Toronto)
🏢 Siena AI
📍 Toronto