Siena AI

Head of Strategic Accounts

Siena AI • $120K — $180K *
New York, NY 10025In-Person
Business Services
Less than 5 years of experience
4 days ago
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Job Overview by Ladders

Qualifications

  • 5-7 years of experience in enterprise account management
  • Strong commercial track record with measurable revenue achievements
  • Experience managing C-level conversations that drive results
  • Ability to navigate complex multi-stakeholder organizations
  • Proven success in winning back at-risk accounts against competition
  • Familiarity and active use of AI tools in business strategies
  • Leadership skills with a hands-on approach in team collaboration

Responsibilities

  • Own a portfolio of strategic accounts, ensuring retention and expansion
  • Develop stakeholder maps to identify key decision makers
  • Lead multi-team expansion efforts beyond traditional buying centers
  • Conduct executive-level conversations to drive meaningful contracts
  • Collaborate with AEs on commercial strategies and PMs on product roadmaps
  • Reclaim at-risk accounts through effective, value-driven discussions
  • Create a foundational playbook for strategic account management

Benefits

  • Remote-first working arrangement with occasional customer travel
  • Influential role in shaping Siena's strategic direction
  • Fast-paced team culture that values customer success as a growth function
  • Equity options included, aligning personal success with company growth
Full Job Description
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

About Siena AI

Siena AI is a developer of an autonomous chat platform that aims to transform the way it runs and interacts with consumers by combining human empathy and intelligent automation. The platform provides capabilities such as product information, order tracking, address changes, returns and product exchanges, subscription and retention management, allowing firms to conduct customer care and social media interactions autonomously.

Siena AI Careers

There has never been a better time to join the global team of Siena AI professionals, a leading force in the artificial intelligence sector.

Work You'll Do

Join Siena AI's market-leading team to assist some of the most innovative companies in mastering their technology-driven transformation journeys. At Siena AI, the fusion of technology, industry expertise, and digital innovation puts the company at the forefront of the AI industry. Lead in a unique market position, harnessing the power of AI to drive industry-wide changes and deliver unparalleled innovation. Engage with a global team of business and technology advisors, helping clients navigate through complex AI integrations and transformations. Collaborate with a dedicated group of AI experts, driving forward the boundaries of what's possible in technology and business.

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This team is dedicated to building a leading advisory service, guiding major companies through their digital transformation journeys using advanced AI solutions.

Innovative Work

Be part of the largest group of AI professionals, delivering targeted solutions through a depth of consulting experience and innovation that is unmatched in the industry.

Innovate and Grow

Deliver solutions that are trusted by enterprises worldwide, leveraging Siena AI's extensive consulting experience and innovative approaches.

Be Part of a Great Team

Join a team that works on cutting-edge Microsoft technology and harnesses the capabilities of a global scale operation to develop joint solutions.

Future-Proof Your Career

With Siena AI, go as far as ambition can take, with endless opportunities to advance careers through unmatched training, development, and certification support.

Explore Job Opportunities

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The Siena AI Leadership and Innovation

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Learn more about Siena AI
Size
11 employees
Industry
Information Technology
* Ladders Estimates

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