Rollstack is solving the last mile problem in the modern data stack and creating a new category: Reports Automation. We connect BI tools to slide decks and documents, automating their generation and updates.

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 Company

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 a driven and customer-obsessed Senior Solutions Engineer to lead technical engagements across the entire customer lifecycle—from pre-sales discovery to post-sale onboarding and strategic expansion.

This role is perfect for someone who thrives at the intersection of product and go-to-market, enjoys working directly with customers, and excels at simplifying complex technical concepts into clear, actionable solutions.

As a Senior Solutions Engineer, you’ll be a critical player in helping prospects understand the value of Rollstack, guiding new customers through implementation, and enabling our Sales and Customer Success teams with scalable technical tools and content. You’ll collaborate closely with Product, Engineering, and DevOps to ensure our customers and field teams are set up for long-term success.

What You Will Do

As a Solutions Engineer at Rollstack, you’ll be the technical partner across the entire customer journey—pre-sales, onboarding, and ongoing success—while enabling our GTM team and shaping product strategy.

Pre-Sales & Evaluations

• Partner with sellers to lead technical discovery, solution design, and InfoSec/security reviews.
• Own responses to security questionnaires and collaborate with Product and Engineering as needed.

Onboarding & Implementation

• Guide new customers through technical setup, including data source (DS) connections and custom network configurations.
• Coordinate with DevOps and establish collaboration channels (Slack/Teams) with clients to ensure smooth onboarding.

Post-Sales Support

• Assist with platform configuration, onboarding additional users, and advising on best practices for long-term success.

GTM & Technical Enablement

• Serve as the technical subject matter expert across GTM, developing internal documentation and training programs for Sales, Marketing, and Customer Success.
• Lead high-impact, tailored product demos across industries, personas, and use cases.
• Maintain and evolve demo environments, scripts, and a scalable modular demo framework.
• Train internal teams and certify them on demo delivery standards.

Work Cross-functionally

• Consolidate feedback from the field to inform roadmap planning and highlight blockers or recurring customer needs.
• Track trends in evaluations and usage to support GTM strategy.
• Collaborate with Marketing to create and maintain technical sales assets, including decks, diagrams, one-pagers, and demo content.
• Review outbound messaging for technical accuracy and consistency.

Who We Are Looking For

We’re looking for a well-rounded Senior Solutions Engineer who blends technical expertise with strong communication skills and a deep sense of customer empathy. You’re excited to work cross-functionally and build scalable systems in a fast-paced environment.

• 3–6 years of experience in Solutions Engineering, Sales Engineering, or a similar technical customer-facing role.
• A solid understanding of software architectures, APIs, and enterprise software ecosystems.
• Familiarity with the data and analytics landscape, including experience with BI tools such as Looker, Power BI, Tableau, Snowflake, or BigQuery.
• Proven experience supporting pre-sales, onboarding, and post-sales technical enablement.
• Strong demoing and storytelling skills—able to tailor technical narratives to both business and technical stakeholders.
• Ability to collaborate effectively across Sales, Marketing, Product, and Engineering teams.
• A self-starter attitude with a focus on building repeatable, scalable processes and content.

Bonus Points For:

• Experience working in high-growth SaaS or startup environments.
• Knowledge of InfoSec and enterprise procurement processes.
• Comfort building and managing demo environments or internal enablement programs.

Why Join Us

• Join a Y Combinator-backed company that’s redefining how individuals and teams—across industries and around the world—work smarter and faster.
• Work alongside an exceptional team of builders and operators, including alumni from Amazon, Pinterest, Tesla, Nvidia, and AiFi.
• Be part of a fully remote, globally diverse workplace that values autonomy, impact, and collaboration.
• Contribute to a product that users love and that truly sells itself—built by a world-class product and engineering team.
• Look forward to bi-annual team offsites in destinations that belong on your travel bucket list.
• Earn competitive compensation and meaningful equity in a fast-moving, high-leverage startup where your work directly shapes the company’s trajectory.