Senior Deal Desk Analyst

Bask is the best telehealth platform on the market. Our mission is to empower entrepreneurs and businesses to launch a DTC telemedicine company quickly and easily, abstracting away the complexities of the industry into an easy-to-use platform. With hundreds of features to meet the unique needs of telehealth, we put all the tools in our customers' hands for success. We are a rapidly growing startup, and we work with care and intention to create a high-performance company with the following in mind:

• Speed Wins. Make decisions, move quickly, and know that if things go wrong, it's okay for you and the company.
• Intuition, Then Data. We're a data-driven company. We start with our instincts and then use data to validate our decisions and improve.
• Miles, Not Inches. Thinking small is a self-fulfilling prophecy. Favor bold ideas over incremental changes.
• Customer-Obsession. We are obsessed with helping all our customers launch multi-billion-dollar companies with ease. We accomplish this by knowing our customers incredibly well and finding ways to make their businesses better.
• Ownership & Accountability, together. We embody a culture of extreme ownership, accountability, and teamwork. We count on every team member to take responsibility for their work, embrace a proactive mindset to overcome challenges, and work together to achieve our collective success.

A look into the day to day:

• Own the deal review and approval process, helping our Sales team structure and close deals accurately and efficiently.
• Partner with Sales, Finance, Legal, and other teams to support pricing, contracts, and commercial decisions.
• Build and improve the processes, systems, and workflows that make deal execution faster and more scalable.

We're Looking For

We're looking for someone who is detail-oriented, commercially minded, and comfortable navigating complex deal structures. You understand how sales processes work, can balance business needs with operational and financial considerations, and know how to find practical solutions when situations don't fit neatly into a standard process. You're proactive, resourceful, and enjoy building structure in a fast-moving environment.

Deal Desk at Bask Health is AI-first and customer-obsessed. Work starts in an LLM to clarify intent and context, moves into deal analysis, commercial workflows, and cross-functional execution, is validated against real business needs and outcomes, and is continuously refined as we learn. AI and self-serve research are default parts of the workflow, not side experiments.

We are looking for Deal Desk professionals who take full ownership of deal execution and operational excellence, treat AI as a real collaborator, and care deeply about helping our teams close business efficiently while protecting the long-term interests of the company and our customers.

What You'll Do

• Work AI-first: Use AI and automation to research, analyze, and improve deal workflows, reducing manual work and increasing accuracy.
• Own deal reviews, approvals, deal structuring, and quote configuration from initial review through contract execution.
• Partner with Sales to provide guidance on pricing, deal terms, non-standard requests, and commercial strategy.
• Work closely with Finance, Legal, Product, and other teams to support new pricing, packaging, and product launches.
• Monitor deal data and performance to identify trends, improve sales execution, and reduce operational risk.
• Identify opportunities to streamline processes, improve documentation, and automate repetitive work.
• Create clear playbooks and training materials that help the Sales team navigate deal processes.
• Share effective AI-native workflows and operational improvements across the team.

In This Job, You Will:

• Manage the day-to-day deal review and approval process, ensuring deals are structured accurately and completed on time.
• Review pricing, quotes, contract terms, and commercial requirements, escalating issues when needed.
• Serve as a trusted resource for Sales, helping teams navigate complex or non-standard deal scenarios.
• Maintain accurate opportunity and deal data, supporting financial reporting, forecasting, and revenue integrity.
• Partner with Finance and other stakeholders on deal audits and process controls.
• Support the rollout of new pricing structures, packaging, sales programs, and commercial processes.
• Analyze deal performance and identify opportunities to improve sales velocity and reduce business risk.
• Translate operational needs into clear requirements for systems, tooling, and automation.
• Find comfort in working in a fast-paced startup environment.
• Believe no task is too small and no ask is too tall

Requirements

• 4+ years of experience in Deal Desk, Pricing, Quote-to-Cash, Contract Management, Revenue Operations, Sales Operations, or a related function within the technology sector.
• Experience partnering with Sales teams and cross-functional stakeholders to move complex deals forward.
• Strong understanding of deal structures, commercial processes, and the operational considerations involved in closing business.
• Demonstrated experience managing projects and improving business processes.
• Strong analytical and critical-thinking skills, with the ability to assess downstream impacts and make sound decisions.
• Excellent communication and collaboration skills, with a customer-service mindset when supporting internal teams.
• Resourceful, proactive, and comfortable solving problems independently in ambiguous situations.
• Ability to manage multiple priorities while maintaining accuracy and attention to detail.
• Experience with Salesforce CPQ or a comparable CPQ platform is a plus.
• Experience using AI or automation to improve operational workflows is a plus.