Account Executive

Rollstack; New York (NY); On-site; CAD 90,000 - 150,000; Full time

Job summary

Rollstack is redefining how organizations communicate data by automating executive reporting and presentations. We seek an Account Executive who can diagnose complex workflows and engage senior stakeholders to rethink how reporting gets done.

You will own the full sales cycle, engage data, analytics, and finance teams, and collaborate with leadership to scale our go-to-market motion. Strong communication and ownership are essential in a fast-moving startup.

Qualifications

• Experience in enterprise software, analytics, data, consulting, or customer-facing roles.
• Deep understanding of analytics, BI, reporting, or operational workflows.
• Strong communication with senior stakeholders and cross-functional teams.

Responsibilities

• Own the full sales cycle from prospecting through close for mid-market and enterprise accounts.
• Engage with data, analytics, finance, operations, and executive stakeholders.
• Lead discovery conversations around reporting workflows and executive communication.
• Guide customers through evaluations, pilots, and deployments.
• Collaborate with Engineering and Product during evaluations and security reviews.
• Develop multi-threaded relationships across customer organizations.
• Work with CEO on strategic opportunities and large enterprise accounts.
• Refine Rollstack’s sales motion, messaging, and playbooks.
• Maintain pipeline management and operational discipline.

Skills

Strong communication

Executive presence

Problem solving

Ownership mentality

Startup environment

Tools

Tableau

Sigma

ThoughtSpot

Looker

Power BI

Snowflake

Job description

The Company

The Company

At Rollstack, we are redefining how organizations communicate data. Companies invest millions into dashboards and analytics platforms, yet the most important decisions still happen through slide decks, documents, and executive reporting workflows. Leadership reviews, board decks, QBRs, operating reviews, investor updates, customer presentations — these workflows remain painfully manual inside even the most sophisticated organizations. Rollstack automates that last mile. We work with leading organizations ranging from fast-growing companies to enterprises like SoFi, Zillow, and Whirlpool to automate data-driven presentations and documents directly from tools like Tableau, Power BI, Looker, and Excel. Headquartered in New York, Rollstack is remote-first and backed by Insight Partners and Y Combinator. We operate with high intensity, high ownership, and high standards. We care deeply about craft, speed, and customer impact. We value intelligence, humility, curiosity, and people who want to build category-defining companies.

About The Role

This is not a traditional SaaS AE role. Rollstack sits at the intersection of analytics, executive communication, operations, and workflow automation. Selling Rollstack requires deeply understanding how organizations consume data — not just running a generic sales process. We are looking for highly consultative, intellectually curious Account Executives who can diagnose complex reporting workflows, engage senior stakeholders, and help customers rethink how executive reporting gets done inside their organizations. The ideal candidate is not just a “closer.” They are a strong operator, communicator, and problem solver who enjoys going deep with customers and navigating complex environments.

Ideal Experience

• Tableau, Sigma, ThoughtSpot, Looker, Power BI, or modern data platforms
• Management Consulting, Finance, Investment Banking, or other Strategy & Operations roles
• Analytics or Data consulting
• Technical pre-sales or customer-facing analytics roles looking to move into a commercial ownership role

You will work directly with the CEO and leadership team on key accounts and play a pivotal role in shaping how Rollstack scales its go-to-market motion.

What You Will Do

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

Who 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, or operational workflows
• Exceptional communication skills, both written and verbal
• Executive presence and ability to engage senior stakeholders credibly
• Strong intellectual curiosity and structured problem-solving ability
• High ownership mentality with strong attention to detail
• Comfortable operating in fast-moving, ambiguous startup environments
• Ability to balance technical depth with commercial execution
• Strong work ethic and bias toward action

Strong Plus

• Background in engineering, finance, management consulting, or investment banking.
• Experience with the data stack: Tableau, Sigma, ThoughtSpot, Looker, Power BI, Snowflake, or modern data ecosystems
• Experience in Analytics, Consulting, or Operational Strategy roles
• Experience selling workflow-oriented or highly consultative products
• Startup experience