About the role

Role: Account Executive (Consultative, Workflow-Focused)

Rollstack is looking for a highly consultative Account Executive who understands how organizations consume data and how executive reporting workflows work end-to-end. This is not a traditional SaaS AE role—your success depends on diagnosing complex reporting and communication processes and helping customers rethink how executive reporting is done.

What you’ll do

Own the full sales cycle from prospecting through close for mid-market and enterprise accounts
Conduct highly consultative discovery around reporting workflows, executive communication, and operational processes
Engage senior stakeholders across data, analytics, finance, operations, and executive teams
Guide customers through evaluations, pilots, and deployments
Partner with Engineering and Product during technical evaluations, security reviews, and implementation planning
Build multi-threaded relationships across customer organizations
Collaborate directly with the CEO on key accounts and strategic opportunities
Refine Rollstack’s sales motion, messaging, and playbooks
Maintain rigorous pipeline management and operational discipline

What we’re looking for

3+ years of experience in enterprise software, analytics, data, consulting, or customer-facing technical roles
Strong understanding of analytics, business intelligence, reporting, and operational workflows
Exceptional written and verbal communication and executive presence
Intellectual curiosity and structured problem-solving
High ownership and strong attention to detail
Comfort operating in a fast-moving, ambiguous startup environment
Ability to balance technical depth with commercial execution

Strong plus / preferred background

Finance, Investment Banking, or Management Consulting experience
Familiarity with the data stack (e.g., Tableau, Sigma, ThoughtSpot, Looker, Power BI, Snowflake, modern data ecosystems)
Experience selling analytics/workflow automation or operational strategy solutions

About Rollstack

Rollstack automates the “last mile” of executive data communication. Instead of relying on manual slide decks, board decks, QBRs, and reporting workflows, it generates data-driven presentations and documents directly from tools like Tableau, Power BI, Looker, and Excel. The company is remote-first, based in New York, and backed by Insight Partners and Y Combinator.