Director, Strategic Accounts

About the role

Siena is at the forefront of transforming customer service through its innovative Agent of Record platform, which streamlines various customer service functions into a cohesive and intelligent solution. We are in search of an experienced leader to oversee our most valuable accounts and help define our long-term commercial vision. This position reports directly to the CEO and Co-Founder, and you will play a crucial role in driving growth within our most intricate enterprise client relationships. You will own the end-to-end strategic direction for our highest value clients, acting as the primary executive voice for Siena within their organization. This role requires a unique blend of visionary strategy and hands-on execution to navigate complex buying committees. You will be responsible for architecting long-term account plans that align with both client objectives and our company goals. The position demands comfort in operating at the highest levels of corporate decision-making while maintaining granular insight into account health. You will translate broad market trends into specific actions that secure expansion and deepen partnerships. Ultimately, this role is about building enduring trust and ensuring our marquee clients derive maximum value from our platform.

Key facts

What you'll do

• Orchestrate a portfolio of accounts generating over $100,000 in annual recurring revenue, driving strategic initiatives and ensuring sustained satisfaction.
• Spearhead high-level executive dialogues with C-suite stakeholders to secure contract renewals and uncover new commercial expansion vectors.
• Dissect and diagram stakeholder ecosystems within target organizations to reveal latent opportunities across marketing, e-commerce, and operational verticals.
• Synthesize product feedback from client engagements and channel these critical insights directly to the engineering leadership for rapid iteration.
• Engineer bespoke strategies to intercept accounts facing churn risks and outmaneuver competing solutions through value-centric engagement frameworks.
• Author and institutionalize a comprehensive strategic account playbook, establishing foundational best practices and governance models from inception.
• Harmonize cross-functional teams around unified strategic initiatives, ensuring client requirements are addressed with precision and agility.
• Scrutinize competitive movements and industry evolutions to inform proactive strategic decisions and preserve a distinct market advantage.
• Cultivate and sustain high-trust relationships with key decision-makers to foster long-term collaboration and mutual success.
• Compile and deliver executive-level reports on account performance, roadmap alignment, and strategic initiative outcomes to the C-suite.
• Facilitate immersive training workshops for internal team members on advanced account management and engagement methodologies.
• Mentor emerging account managers, instilling a performance-driven culture that prioritizes continuous learning and developmental excellence.

Requirements

• Demonstrate a proven track record in managing revenue streams, including successful upselling, cross-selling, and renewing contracts with measurable, quantifiable success.
• Exhibit experience in navigating complex enterprise environments characterized by multiple stakeholders and extended sales cycles spanning considerable duration.
• Possess a strong ability to engage effectively with C-suite executives and VP-level stakeholders to drive impactful, value-based business outcomes.
• Provide evidence of demonstrated success in recovering at-risk accounts and overcoming entrenched competitive challenges through strategic intervention.
• Show technical proficiency with AI-native tools such as Claude Code, accompanied by tangible evidence of personal projects or meaningful contributions to internal operating systems.
• Embrace a player-coach mindset that enables hands-on execution during critical calls while simultaneously developing scalable processes that empower the broader team.
• Hold a deep understanding of the nuances involved in managing strategic enterprise accounts within a B2B SaaS context.
• Adhere to strict confidentiality and discretion when handling sensitive client information and strategic business data.

Nice to have

• Bring prior experience within the technology or SaaS industry, specifically within customer service solution ecosystems.
• Demonstrate familiarity with leading CRM systems and sophisticated account management software platforms.
• Highlight previous experience thriving in fast-paced startup environments, showcasing adaptability, resourcefulness, and resilience.
• Leverage knowledge of data analytics tools to track intricate account performance metrics and derive actionable, data-driven insights.
• Maintain an established network of contacts within the enterprise sector capable of facilitating tangible business development opportunities.

Practical notes

• This position is designated as fully remote, though occasional travel may be necessary to meet with key customers at strategic intervals.
• Please note that we utilize AI-assisted screening for job applications; if you prefer a human-only review of your materials, kindly reach out to talent@siena.cx to request an alternative process.
• Siena is an equal opportunity employer dedicated to fostering diversity, equity, and inclusion throughout all levels of the organization.

This role represents a pivotal opportunity to shape the future of a high-growth company that is redefining customer service automation. The Director, Strategic Accounts will be instrumental in bridging the gap between ambitious product innovation and the real-world application for leading brands. Success in this position requires a rare combination of analytical rigor, interpersonal acumen, and operational discipline. You will not only manage relationships but also influence the strategic trajectory of the company by articulating client needs and market demands. The ideal candidate views challenges as opportunities to create scalable, value-rich solutions for both the client and the business. This is a leadership position that demands ownership, creativity, and a relentless focus on results. Joining Siena means joining a mission to transform how businesses interact with their customers in the digital age. Your strategic input will directly impact revenue retention and expansion, positioning the company for sustained market leadership. We seek a proactive individual who can balance big-picture thinking with meticulous execution. If you are driven by building long-term partnerships and leveraging technology to solve complex business problems, this role is the perfect alignment. Apply if you are ready to take on significant responsibility and contribute to a mission-driven organization that values innovation and collaboration above all else.