[![Image]() Meet Jobicy Copilot — free AI autofill for job applications + remote job alerts ›](#) [All remote jobs](https://jobicy.com/jobs.md)Open role[![RStudio logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/7c5f8854-221.jpg)](https://jobicy.com/company/rstudio.md)Remote opportunity at[RStudio](https://jobicy.com/company/rstudio.md) # Director, Enterprise Sales Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/rstudio.md)Share2 Sep 2026Published31Listing views3Application actions2 Oct 2026Apply before Opportunity details ## About this role. AI SummaryPosit is hiring a Director of Enterprise Sales to lead its land-and-expand strategy within large existing customers of its data science platform. The role manages and mentors at least five Enterprise Account Managers while establishing value-realization practices, account expansion motions, and disciplined forecasting. This leader will support complex enterprise license negotiations, collaborate with Customer Success and Solutions Engineering, and help sellers reach CIO and CDO stakeholders. The position is US-remote within Posit’s distributed organization, with the option to work from its Boston office. Compensation is disclosed as a US hiring range that includes base salary and commission. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior revenue leadership position requiring ownership of a repeatable expansion model, management of a sales team, and executive-level involvement in complex enterprise negotiations. Success depends on combining rigorous forecasting and SaaS metrics with strong cross-functional influence and strategic account leadership. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianHighly competitive$372,780US market range$280k–$450k0$495k AI insightThe disclosed yearly hiring range is $321,400 to $424,160 USD and explicitly includes base salary and commission; its midpoint is $372,780 USD. This sits within a competitive US-market range of roughly $280,000 to $450,000 USD in annual total compensation for a Director-level enterprise SaaS sales leader, with actual earnings varying based on team scope, quota design, commission mix, and enterprise sales experience. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise%20Sales.md)[SaaS Sales Leadership](https://jobicy.com/jobs?search_keywords=SaaS%20Sales%20Leadership.md)[Land and Expand](https://jobicy.com/jobs?search_keywords=Land%20and%20Expand.md)[Account Management](https://jobicy.com/jobs?search_keywords=Account%20Management.md)[Sales Forecasting](https://jobicy.com/jobs?search_keywords=Sales%20Forecasting.md)[Enterprise Negotiation](https://jobicy.com/jobs?search_keywords=Enterprise%20Negotiation.md)[Revenue Expansion](https://jobicy.com/jobs?search_keywords=Revenue%20Expansion.md)[Salesforce](https://jobicy.com/jobs?search_keywords=Salesforce.md)[Team Mentorship](https://jobicy.com/jobs?search_keywords=Team%20Mentorship.md)[Cross-Functional Collaboration](https://jobicy.com/jobs?search_keywords=Cross-Functional%20Collaboration.md) Sample interview questionsHow would you build a repeatable land-and-expand playbook for Global 2000 accounts?I would begin by segmenting accounts according to adoption maturity, renewal timing, technical health, stakeholder coverage, and expansion potential. I would define stage-based actions for identifying advocates, quantifying value, mapping executive buyers, and creating mutual expansion plans, then operationalize those actions in Salesforce with clear inspection metrics. How do you create a no-surprises forecast while managing both renewals and expansion? I use a consistent forecast cadence that separates committed renewals, risk exposure, qualified expansion, and upside. Forecast confidence should be evidence-based, including decision process, executive sponsor alignment, technical validation, procurement status, and documented next steps; I also inspect risks early and assign concrete mitigation plans. Describe your approach to coaching Enterprise Account Managers to sell higher in an organization. I coach sellers to connect technical usage to executive priorities such as governance, standardization, cost efficiency, risk management, and business outcomes. We prepare stakeholder-specific hypotheses, multithread relationships across technical and business functions, and use value reviews to earn access to CIO, CDO, and procurement leaders. How would you support a complex enterprise license agreement exceeding $250,000? I would align the account team around the customer’s strategic outcomes, commercial objectives, decision criteria, and negotiation plan before entering late-stage discussions. During the deal, I would coordinate executive sponsorship, solutions validation, legal and procurement engagement, and concession strategy while protecting long-term expansion potential. What metrics would you use to evaluate the performance of an enterprise expansion team? I would track net revenue retention, renewal rate, expansion pipeline coverage, win rate, deal cycle time, forecast accuracy, account penetration, and executive relationship coverage. I would pair these lagging indicators with leading measures such as value reviews completed, mutual success plans, multithreaded stakeholder maps, and identified seat-expansion opportunities. At Posit, our “Land and Expand” motion is our greatest engine for growth. This team is dedicated to uncovering new value within our largest existing customers, transitioning departmental users into enterprise-wide adopters of our professional data science platform. You will be the architect of our expansion playbook—defining how we move from a small cluster of R or Python users to a centralized, IT-blessed data science infrastructure. ### What You’ll Own: * The Expansion Playbook: Singularly responsible for formalizing the “Advocacy Bridge,” value realization strategies, and the operational rigor required to turn product usage into business-critical infrastructure. * Team Performance & Mentorship: Lead, mentor, and professionalize a team of at least five Enterprise Account Managers (EAMs) in a high-growth SaaS environment. * Predictable Forecasting: Instill the rigor necessary to provide the CSO with a “no-surprises” forecast, balancing renewal risks with expansion upside. ### What You’ll Assist With: * High-Value Negotiations: Support the team in the trenches on deals exceeding $250k+, helping architect Enterprise License Agreements (ELAs). * Cross-Functional Collaboration: Act as the primary bridge between Sales, Customer Success, and Solutions Engineering to ensure technical health leads to commercial growth. * Global Account Mapping: Collaborate with EAMs to proactively hunt for the next 100+ seats within Global 2000 accounts. ### What You’ll Teach: * “Up and Out” Navigation: Teach sellers how to move from a technical user base to the CIO/CDO office. * SaaS Sales Math: Provide expertise in managing by the numbers and maintaining deep proficiency in Salesforce. * Land and Expand Mechanics: Share proven strategies for increasing Net Revenue Retention (NRR) year-over-year. ### What You’ll Learn: * Posit’s PBC Values: Understand how to represent Posit’s unique Public Benefit Corporation mission within a high-performance sales culture. * Technical Product Nuance: Deepen knowledge of the specific transition from R/Python clusters to centralized data science infrastructure. Posit offers competitive compensation with extensive human-first, people-focused benefits to prioritize your personal and financial well-being. Individual pay decisions are based on a number of factors, including qualifications for the role, experience level, and skillset. The hiring range includes base salary and commission. In addition, we offer an annual cash bonus, targeted at 10% of base pay, that pays out based on company performance and a cash grant that vests over 4 years. This hiring range assumes that the job will be performed in the United States. Hiring range $321,400—$424,160 USD ### Working at Posit: * We welcome all talented colleagues and are committed to a culture that represents diversity in all its forms. * We prioritize giving ourselves “focus time” to get deep work done. We minimize meetings and attempt to operate asynchronously. * We are a learning organization and take mentorship and career growth seriously. We hope to learn from you and we anticipate that you will also deepen your skills, influence, and leadership as a result of working at Posit. * We operate under a unique sustainable business model: We have over 50% of our engineering dedicated to creating free and open source software. We are profitable and we plan to be around decades from now. * Posit is a Public Benefit Corporation (PBC) and a Certified B Corporation®, which means our open-source mission is codified into our charter. As a result, our corporate decisions balance the community’s interests, customers, employees, and shareholders. Hear more about why we think this matters[here](https://blog.rstudio.com/2020/01/29/rstudio-pbc/). ### Notable: ### We offer competitive compensation with extensive human-first, people-focused benefits to prioritize your personal and financial well-being. These benefits apply to full-time positions only. * 100% of medical, dental, and vision insurance premiums are covered for employees and their families! Fertility and gender-affirming healthcare is included in all of our plans. * Supplemental mental health and wellness benefits are available via Ginger even if you don’t opt in to our insurance plans, including Ginger for teen family members. * Posit’s gender-neutral paid parental leave policy covers all new parents, including foster and adoptive parents. * All full-time employees are eligible for 401k enrollment starting on day one. * After six months of employment, Posit provides a substantial yearly match to employee 401K contributions. * An annual profit-sharing bonus for employees recognizes our team’s contributions to company performance across the year. * We are a 100% distributed team. You are also welcome to come into our Boston office. * We offer a $400 monthly reimbursement for coworking space rental if you prefer to work away from home. * Our Lifestyle Savings Account offers an initial deposit of $1800 and then an additional quarterly stipend of $375 to cover the costs of professional development, wellness, financial health, charitable giving, and remote work support. * We provide a flexible environment with a generous vacation policy that encourages a minimum of four weeks PTO per year plus 15 paid company holidays. Are you excited about this role but not sure if your experience aligns with every qualification in the job description? That’s okay. We know multiple perspectives are essential for a thriving organization and we’d still love to hear from you! Posit is committed to being a diverse and inclusive workplace. We encourage applicants of different backgrounds, cultures, genders, experiences, abilities, and perspectives to apply. All qualified applicants will receive consideration for employment without regard to race, color, national origin, religion, sexual orientation, gender, gender identity, age, physical disability, or length of time spent unemployed. Posit Software, PBC participates in the federal E-Verify program, which confirms employment authorization of newly hired U.S. based employees. E-Verify is not used as a tool to pre-screen candidates and is only initiated upon hire. [E-Verify Participation Notice](https://posit.co/wp-content/uploads/2023/11/E-Verify_Participation_Poster_Eng_Es.pdf) (English/Spanish) [Right to Work Notice](https://posit.co/wp-content/uploads/2023/11/IER_RightToWorkPoster_Eng_Es.pdf) (English/Spanish) #LI-REMOTE Show more [Apply now >](https://jobicy.com/jobs/152371-director-enterprise-sales-2.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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