Who you are

- Shark mindset: commercially driven, first-principles operator - not someone who runs a playbook they inherited

- Commercial track record: quota carried or measurable revenue owned - upsells, cross-sells, expansions, renewals, hard numbers

- C-level presence: you've run conversations with C-suite/VP stakeholders that moved contracts, not just maintained the relationship

- Enterprise account complexity: multi-stakeholder orgs, relationships that compound over years

- Account win-back: you've pulled accounts back from the edge and beaten competitors head to head

- AI-native, not AI-curious: you're actively building with tools like Claude Code and can show real projects - you'll be contributing to our internal OS

- Player-coach: in the room, on the calls, building the playbook from what you do

- 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

What the job involves

- Our strategic accounts, brands at $100K+ ARR, are the foundation of Siena's growth

- This is the forward-deployed motion: deep, multi-year relationships where the work is less "check-in" and more "co-build"

- You'll own a portfolio of our highest-value customers, lead the relationships from the executive level,



and drive the cross-functional expansion that turns a single CX deployment into connective tissue across a customer's entire business

- This is a permanent, senior operator and leadership role reporting to our CEO/Co-Founder

- You'll work in close partnership with our AEs on commercial expansion and with our PMs on roadmap influence

- Own a portfolio of strategic accounts ($100K+ ARR), driving retention, expansion, and executive relationships

- Build stakeholder maps: who matters, where decisions get made, where Siena can expand next

- Lead multi-team expansion, beyond the CX buying center into Marketing, Returns, E-commerce, Operations

- Run executive-level strategic conversations that move contracts and direction — this is about commercial outcomes, not calendar touch-points

- Partner with AEs on multi-team commercial expansion; partner with PMs to translate account needs into roadmap influence

- Win back at-risk accounts and defeat competitive threats through value-led conversations

- Build the playbook for how Siena operates in strategic accounts from first-principles, not from importing what you did elsewhere

Benefits

- ? The flexibility to work from anywhere

- ? Adaptable working hours

- ? Stock options

- ? Unlimited PTO (minimum of 15 days off per year)

- ? Growth stipend

📌 Director of Strategic Accounts (Canada)
🏢 Siena
📍 Canada