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 rapid-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.

This role is ideal for someone coming from: 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 the 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 Finance, Investment Banking, Management Consulting

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

📌 Account Executive (Canada)
🏢 Rollstack
📍 Canada