Head of Strategic Accounts

Siena AI•New York, NY

1d•Remote

About The Position

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.

Requirements

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

Responsibilities

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

Competitive base salary + equity
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
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.