Director, Strategic Accounts
At a glance
Leadership Account Management role at Siena AI. Remote, United States · full-time.
Pay not stated
Growth Roles summary, based on the employer's posting.
What you'll do
- Own high-value strategic accounts, protecting renewals while finding expansion opportunities and maintaining executive relationships
- Map decision-makers across customer organizations to identify influence paths and where additional deployments could grow
- Lead expansion beyond CX into Marketing, Returns, E-commerce, and Operations teams
- Run senior commercial discussions, recover threatened accounts, and counter competitors through value-based conversations
- Shape the strategic-account playbook while coordinating with AEs on deals and PMs on product direction
What you bring
- A proven commercial record with quota ownership or measurable revenue from upsells, cross-sells, expansions, or renewals
- Experience leading C-suite or VP conversations that changed contract outcomes, rather than simply maintaining contacts
- Background handling complex enterprise accounts with many stakeholders and relationships developing over multiple years
- Hands-on experience creating with AI tools such as Claude Code, supported by real projects
Who this fits
You’ll suit a commercially forceful senior operator who can work directly with executives, build structure from scratch, and act without daily oversight. The role is remote for someone in New York and reports to the CEO/Co-Founder. It is a player-coach position: you’ll stay active in customer calls while creating the operating playbook.
From the employer
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
Our strategic accounts, 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 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 role reporting to our CEO/Co-Founder, working closely with AEs on commercial expansion and PMs on roadmap influence.
What You'll Do
Own a portfolio of strategic accounts (those paying us $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
Who You Are
The Bar: if you're missing any of these, this isn't the role for you:
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
Strong Signal: not dealbreakers, but what separates a good hire from a great one:
Shark mindset: commercially driven, first-principles operator, not someone running an inherited playbook
Account win-back: you've pulled accounts back from the edge and beaten competitors head to head
Player-coach: in the room, on the calls, building the playbook from what you do
AI-native, not AI-curious: you're actively building with tools like Claude Code and can show real projects
Nice to Have: bonus, not required:
Experience in e-commerce or consumer brands specifically, not just B2B SaaS
You've built a strategic accounts function from zero rather than inherited one already running
Existing relationships among CX or ops leaders at consumer brands
Not a Fit If
You want a playbook handed to you rather than building one
You're better at maintaining relationships than driving hard commercial conversations
You need daily oversight or a defined process before you act
Why Siena?
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.
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 a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows.
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.
How we hire
We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx.
Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
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