About the role

Role overview

Join Siena as Director of Strategic Accounts to lead relationships with the company’s highest-value customers and drive cross-functional expansion. This is a permanent senior leadership role reporting directly to the CEO/Co-Founder, with full remote flexibility.

Key missions

Manage a portfolio of strategic accounts, driving retention, expansion, and executive relationships.
Build stakeholder maps to identify decision-makers and expansion opportunities.
Lead executive-level strategic conversations to influence contracts and commercial direction.

Requirements

C-level presence: you’ve run conversations with C-suite/VP stakeholders that moved contracts, not just maintained relationships.
Enterprise account complexity: experience with multi-stakeholder organizations and long-term relationship building.
Commercial operator mindset (“shark mindset”): first-principles, commercially driven.
Account win-back: track record pulling accounts back from the edge and beating competitors head-to-head.
Proven commercial results: quota carried and/or revenue ownership; measurable performance in renewals, upsells, cross-sells, and expansions.
AI-native: actively building with AI tooling (e.g., Claude Code) and able to show real projects.
Player-coach: hands-on on calls and in-room, contributing to and evolving the playbook.

Nice-to-haves

Contribution to internal operating systems/processes ("internal OS") and willingness to help build the team’s approach from real experience.

About Siena

Siena is a company hiring for senior go-to-market leadership, focusing on expansion with high-value customers. The role description emphasizes enterprise customer relationships and executive-level commercial strategy, indicating Siena operates in a B2B environment where customer growth and retention are key priorities. The posting also references AI-native tooling, suggesting Siena builds and uses modern AI-enabled products or workflows.