Director, Strategic Accounts
About the role
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.
What you'll do
- 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
What we're looking for
- 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
What we offer
- Competitive base salary + equity - we'll size comp to experience
- Remote-first, with occasional travel to customers (especially strategic accounts)
- A seat at the table - this role has real influence over Siena's strategic direction with our most important customers
- A team that moves fast and treats CS as a core growth function, not a support layer