Enterprise Account Executive
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 an Enterprise Account Executive to accelerate our growth across named accounts in the U.S. Central region (preference for candidates based in Chicago or Austin/Dallas metro areas). This role is ideal for a high-performing seller with a strong track record of winning new business, building executive relationships, and positioning product value around strategic outcomes. You’ll be targeting large-scale organizations—primarily those with 10,000+ employees—where business case development, executive alignment, and complex procurement processes are the norm.
Our ideal customers are typically analytics-forward, operationally mature organizations seeking to automate high-frequency reporting workflows—often in finance, strategy, data, sales, or customer success functions.You’ll focus on landing new logos and expanding within key accounts, partnering with data, finance, and operations leaders at some of the most sophisticated companies in the world. 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.You’ll play a key role in shaping how we scale our Enterprise motion and will be responsible for driving revenue against quarterly and annual targets.
What You Will Do
Engage with prospective customers to earn their business and drive contract execution
Own the full sales cycle—from initial engagement to closed-won—including discovery, demo, 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 complex 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 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’re Looking For
6+ years of experience in an Enterprise sales role within a SaaS technology company, preferably in analytics, business intelligence, ML/AI, FP&A, or data-oriented sectors
History of carrying $1MM+ quotas with consistent performance in the top 20% of your peer group
Proven ability to build and execute territory and account plans, with a disciplined approach to prospecting and pipeline development
Strong executive presence with the ability to engage and influence senior decision-makers
Experience closing numerous six-figure deals, with a proven ability to navigate complex decision processes involving multiple stakeholders
Experienced in managing the operational complexity of enterprise deals—including security reviews, legal negotiations, and procurement cycles common to most engagements
Skilled in structured discovery, storytelling, and articulating business value to a diverse set of functional buyers
Holds a high bar for precision—in pipeline hygiene, forecasting, communication, and overall deal execution
Operates with ownership—self-directed and proactive, with a disciplined approach to following a process and a mindset to help improve it as we scale
Familiarity with sales methodologies and qualification frameworks (e.g., MEDDIC, SPICED, or Sandler)
Experience with tools like Tableau, Power BI, Looker, Salesforce, or similar is a plus
Willingness and ability to travel regionally for in-person meetings and events as needed
Brings high ambition, intellectual curiosity, and humility—thrives in a fast-paced, high-ownership startup environment
Why Join Us
Join a Y Combinator-backed company that’s transforming how people — from your friends and family to teams worldwide — work more efficiently.
Collaborate with an exceptional team, including alums of companies like Amazon, Pinterest, Tesla, Nvidia, and AiFi.
Enjoy a fully remote and diverse workplace.
Join a world-class product and engineering team with a product that sells itself.
Participate in bi-annual team offsites at dream destinations from your travel bucket list.
Earn competitive pay and life-changing equity at a fast-growing, high-efficiency startup.
Apply Now