[Hiring] Head of Strategic Accounts @Siena AI

Role Description

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

Qualifications

• 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

Benefits

• 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

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 clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows.