Mid-Market Account Executive

About the Company

At Rollstack, we are revolutionizing the way businesses share and communicate data and insights. Organizations worldwide rely on slide decks and documents to make informed decisions, whether for leadership, clients, or partners. Yet, preparing these materials often consumes countless hours. Rollstack fully automates that.

We help some of the world's leading organizations—from mid-sized to public companies like SoFi, Zillow and Whirlpool—in automating their slide decks and documents. Headquartered in New York, we offer a remote-friendly workplace and are backed by Insight Partners and Y Combinator, the most successful startup incubator in the world that produced the likes of Airbnb, Twitch, Instacart, Dropbox, Reddit, Doordash, Stripe, Coinbase, etc.

Our team operates with speed and focus to deliver outsized impacts for our customers. We approach every challenge with first principles, never assuming things have to be done a certain way. We are a diverse team that believes intelligence and kindness go hand in hand, welcoming individuals from all backgrounds. Our persistence and rapid execution define us as a category leader and a future generational company.

About the Role

Rollstack is seeking a Mid-Market Account Executive to drive growth across accounts in the 1,000–5,000 employee segment. This role is ideal for a high-performing seller who thrives in high-velocity sales environments and has experience navigating multi-stakeholder buying processes. While some deals in this segment may move quickly, many still involve formal evaluations, security reviews, and procurement steps. We’re looking for someone who can manage a variety of deal motions and consistently drive $50k+ ACV relationships—with experience landing six-figure opportunities and a mindset for continuous learning and development.

Our ideal customers are typically analytics-forward, operationally mature organizations seeking to automate high-frequency reporting workflows—often in finance, strategy, data functions, or sales/customer success.

You’ll be responsible for landing new logos and expanding within key accounts, engaging directly with functional leaders in data, finance, and operations at your target accounts. This is a full-cycle, quota-carrying role supported by marketing and a growing GTM engine—but we’re looking for someone who takes ownership of their territory and pipeline with creativity and drive.

What You Will Do

• Engage with prospective customers to earn their business and drive contract execution
• Own the full sales cycle—from initial outreach to closed-won—including discovery, demos, and negotiation
• Develop and execute strategic territory plans to land and expand accounts in your region
• Partner with prospects to define clear business cases and ROI, helping champions secure internal buy-in and budget
• Lead customers through procurement cycles, including security reviews, legal negotiations, and compliance processes
• Build strong, multi-threaded relationships with senior stakeholders across data, finance, and operations
• Collaborate with marketing and leadership to tailor messaging and campaigns for your target accounts
• Accurately manage your pipeline, forecasts, and deal progression using our CRM and sales tools
• Contribute to team-wide knowledge sharing and help evolve our sales playbook as we scale

Who We Are Looking For

• 4–6+ years of experience in a SaaS sales role, with at least 2+ years selling into mid-sized organizations (1,000–5,000 employees)
• Proven track record of carrying a $600k+ annual quota and consistently performing in the top 20% of your peer group
• Strong ability to build and execute territory and account plans, with a disciplined approach to prospecting and pipeline development
• Demonstrated success closing multiple $100k+ deals and consistently landing $50k+ ACV opportunities
• Excellent written and verbal communication skills, with the ability to lead effective demos, craft compelling proposals, and negotiate commercial terms directly with customers
• Experience managing complex sales cycles involving multiple stakeholders—familiarity with legal, security, and procurement processes preferred
• Skilled in structured discovery, storytelling, and articulating business value to a diverse set of functional buyers
• High attention to detail—in pipeline hygiene, forecasting, communication, and overall deal execution
• Self-directed and proactive, with strong ownership and a mindset to improve sales processes as we scale
• Familiarity with sales methodologies and qualification frameworks (e.g., MEDDIC, SPICED, Sandler)
• Experience with BI and CRM tools like Tableau, Power BI, Looker, Salesforce, or similar is a plus
• Willingness to travel occasionally for customer meetings or events
• Brings high ambition, intellectual curiosity, and humility—thrives in a fast-paced, high-ownership startup environment

Why Join Us

• Be part of a Y Combinator-backed company that’s redefining how teams—from executives to analysts—share and act on data
• Work alongside a high-caliber team with experience at Amazon, Pinterest, Tesla, Nvidia, and other top tech companies
• Make a meaningful impact—your work will shape our GTM motion and the outcomes we deliver for customers
• Help scale a category-defining product with a clear use case and strong customer pull
• Thrive in a fully remote, globally diverse work environment
• Build deep relationships in a highly collaborative, high-trust culture
• Participate in bi-annual offsites at inspiring destinations around the world
• Earn competitive compensation and meaningful equity at a fast-growing, capital-efficient startup

1. Screening
2. Behavioral interview
3. Sell me Rollstack
4. Meet the team