Deal Strategy Program Manager at DigitalOcean in Boston, MA

Dive in and do the best work of your career at DigitalOcean. Journey alongside a strong community of top talent who are relentless in their drive to build the simplest scalable cloud. If you have a growth mindset, naturally like to think big and bold, and are energized by the fast-paced environment of a true industry disruptor, you’ll find your place here. We value winning together—while learning, having fun, and making a profound difference for the dreamers and builders in the world. We are seeking a Deal Strategy Program Manager to help us scale how we support our sales organization. This role is a critical partner to sales and collaborates closely with Finance, Legal, and Revenue Operations, helping move deals forward with speed, sound judgment, and operational rigor. Beyond executing day-to-day deal support, this role independently owns complex deals end-to-end, shapes the processes and systems the broader team relies on, and is a go-to resource for less-experienced teammates.

You'll play a central role in structuring deals, improving process quality, and helping our sales team close business efficiently and responsibly. We're looking for someone who operates with real autonomy, exercises sound judgment in ambiguous situations, and is energized by solving problems in a fast-paced environment. This is a strong next step for someone who has built foundational deal desk or revenue operations experience and is ready to own outcomes independently, influence process and policy, and begin mentoring others.

What You'll Do

Own Deal Execution

• Serve as a senior, trusted advisor to Sales leadership and cross-functional stakeholders on structuring and executing complex, non-standard, and high-value deals
• Independently evaluate and resolve non-standard deal requests, driving cross-functional solutions across Sales, Finance, and Legal with minimal oversight
• Own deals end-to-end through quoting, approval, contracting, and quote-to-cash — troubleshooting issues with Finance and Legal with urgency, accuracy, and attention to policy and business context
• Ensure all transactions adhere to internal revenue recognition policies, escalating and resolving edge cases as needed
• Present deal strategy recommendations and insights to senior stakeholders in a clear, concise, data-driven manner

Elevate Operational Quality

• Ensure deal data is complete and accurate in CRM, with a focus on data hygiene and process compliance
• Reinforce and help enforce pricing and discounting governance, exercising judgment in gray areas rather than simply applying rules
• Define requirements for system enhancements (e.g., CRM, CPQ) in partnership with systems and RevOps teams

Drive Process Improvement & Scale

• Proactively identify friction in current processes and lead improvements — including automation and AI (e.g., AI-assisted contract review, quote generation, deal analytics) — to increase speed, consistency, and scale, and reduce manual effort
• Own the optimization of policies, playbooks, and standard operating procedures for deal support, and lead their rollout and adoption across the global team
• Act as a go-to resource for other analysts on sales operations planning, process, and execution

Support & Mentor

• Informally mentor newer Revenue Operations Support Analysts on deal structuring, systems, and policy
• Contribute to internal knowledge-sharing — documentation, training sessions, and onboarding materials — recommending process changes and leading training so improvements scale beyond a single deal

What You'll Add to DigitalOcean

• Business Degree
• 5-7+ years of experience (Deal Desk, Finance, Pricing or Sales Operations experience required), software industry experience preferred.
• Demonstrated experience independently owning complex deals or projects, not just executing defined tasks
• Experience supporting SaaS, cloud, or technology sales organizations
• Strong fluency in systems like Salesforce, CPQ tools, and reporting platforms, with an eye toward data integrity for downstream reporting and forecasting
• Sound judgment for navigating ambiguous or non-standard deal situations, knowing when to escalate versus resolve independently
• A track record of recommending and helping implement process or policy improvements
• Contract management and negotiation experience strongly preferred
• Strong analytical and problem-solving skills with first-principles thinking
• Self-starter mentality with a proactive eagerness to learn, mentor others, and level up the revenue operations team
• Ability to manage multiple priorities and competing stakeholder needs in a fast-paced environment
• Experience using or implementing AI or automation tools (e.g., generative AI, workflow automation, CPQ automation) to improve deal desk efficiency and accuracy a plus

Compensation Range:

• $90,000 - $120,000

*This is a remote role

JR: 2026-8286

#LI-Remote

Why You’ll Like Working for DigitalOcean

• We innovate with purpose. You’ll be a part of a cutting-edge technology company with an upward trajectory, who are proud to simplify cloud and AI so builders can spend more time creating software that changes the world. As a member of the team, you will be a Shark who thinks big, bold, and scrappy, like an owner with a bias for action and a powerful sense of responsibility for customers, products, employees, and decisions.
• We prioritize career development. At DO, you’ll do the best work of your career. You will work with some of the smartest and most interesting people in the industry. We are a high-performance organization that will always challenge you to think big. Our organizational development team will provide you with resources to ensure you keep growing. We provide employees with reimbursement for relevant conferences, training, and education. All employees have access to LinkedIn Learning's 10,000+ courses to support their continued growth and development.
• We care about your well-being. Regardless of your location, we will provide you with a competitive array of benefits to support you from our Employee Assistance Program to Local Employee Meetups to flexible time off policy, to name a few. While the philosophy around our benefits is the same worldwide, specific benefits may vary based on local regulations and preferences.
• We reward our employees. The salary range for this position is based on market data, relevant years of experience, and skills. You may qualify for a bonus in addition to base salary; bonus amounts are determined based on company and individual performance. We also provide equity compensation to eligible employees, including equity grants upon hire and the option to participate in our Employee Stock Purchase Program.
• DigitalOcean is an equal-opportunity employer. We do not discriminate on the basis of race, religion, color, ancestry, national origin, caste, sex, sexual orientation, gender, gender identity or expression, age, disability, medical condition, pregnancy, genetic makeup, marital status, or military service.

Application Limit: You may apply to a maximum of 3 positions within any 180-day period. This policy promotes better role-candidate matching and encourages thoughtful applications where your qualifications align most strongly.