Director, deal desk strategy & operations

📐 About this role

We’re looking for a strategic, collaborative, and results-oriented leader to build and guide our deal strategy & operations function. As the Director of deal desk strategy & operations, you will be a player-coach, responsible for shaping the function's long-term vision while simultaneously rolling up your sleeves to support complex, high-value deals. You will lead a growing team, define our strategic framework for deal execution, and serve as a critical partner to our Go-To-Market (GTM) leadership, all while operating at WRITER speed.

This is a unique opportunity to build a pivotal function from the ground up, establishing the processes, team, and systems that will underpin our commercial success as we scale. You will be a key member of the GTM Strategic Ops leadership team, driving initiatives that help us move faster, adapt to change, and win in the market. We are looking for a leader who embodies our company values of Connect, Challenge, and Own, and who is passionate about building a world-class deal desk organization.

🦸🏻‍♀️ Your responsibilities:

• Drive GTM strategy: act as a strategic partner to Sales, Revenue Operations, BizOps, Finance, Legal, and Product leadership, providing executive-level guidance on complex deal structures, pricing, and non-standard terms to maximize revenue and accelerate deal velocity.

• Lead and mentor: build, manage, and develop a high-performing deal strategy & operations team, fostering a culture of autonomy, high-quality execution, and continuous learning.

• Build scalable processes: design, implement, and optimize the end-to-end quote-to-cash process. You will architect the systems and workflows that enable the team to operate efficiently at scale while maintaining accuracy and compliance.

• Be a hands-on expert: serve as the ultimate point of escalation for the most strategic and complex deals, getting deep in the weeds with your team to find creative solutions and ensure successful closure.

• Generate actionable insights: leverage data from deal cycles to provide the executive team with critical insights that will shape our GTM strategy, influence future pricing and packaging decisions, and inform product development.

• Develop strategic relationships: cultivate strong, trust-based partnerships across the organization, establishing the deal strategy & ops team as the central hub of expertise for all commercial matters.

• Drive quote-to-cash systems strategy: advise on the evolution of our quote-to-cash technology stack, ensuring our tools are optimized for our current needs and prepared for future scale.

⭐️ Is this you?

• Proven experience in a deal desk, sales operations, or revenue operations leadership role, preferably within a high-growth B2B SaaS environment.

• A "player-coach" mindset with a demonstrated ability to lead and mentor a team while also directly contributing to hands-on operational work.

• Deep expertise in structuring complex, multi-product deals, with a strong understanding of revenue recognition principles and commercial legal terms.

• A problem-solving and strategic mindset, with the ability to navigate ambiguity and build new processes and functions from the ground up.

• Excellent interpersonal and communication skills, with the ability to build consensus and act as a trusted advisor to senior leadership.

• Extensive experience with Salesforce CPQ or other quote-to-cash systems.

• A passion for creating an AI-driven operational powerhouse that drives business growth and a reputation for being a collaborative, high-impact leader.

• Experience working with revenue recognition principles and US GAAP.

🍩 Benefits & perks (US Full-time employees)

• Generous PTO, plus company holidays

• Medical, dental, and vision coverage for you and your family

• Paid parental leave for all parents (12 weeks)

• Fertility and family planning support

• Early-detection cancer testing through Galleri

• Flexible spending account and dependent FSA options

• Health savings account for eligible plans with company contribution

• Annual work-life stipends for:

  • Home office setup, cell phone, internet

  • Wellness stipend for gym, massage/chiropractor, personal training, etc.

  • Learning and development stipend

• Company-wide off-sites and team off-sites

• Competitive compensation, company stock options and 401k

WRITER is an equal-opportunity employer and is committed to diversity. We don't make hiring or employment decisions based on race, color, religion, creed, gender, national origin, age, disability, veteran status, marital status, pregnancy, sex, gender expression or identity, sexual orientation, citizenship, or any other basis protected by applicable local, state or federal law. Under the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

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