Enterprise Account Executive - Remote job Sales / Business at Rollstack

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.

• 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

• 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