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PINATA Appoints Rob Olson as Chief Operating Officer to Steer Expansion into AI as TaskFlow Platform Activity Surges
[February 08, 2024]

PINATA Appoints Rob Olson as Chief Operating Officer to Steer Expansion into AI as TaskFlow Platform Activity Surges

PINATA, the innovative TaskFlow orchestration platform for real-world work, announced today that Rob Olson had left the venture firm M13 - where he was a Partner, Head of Data Strategy, and board member to PINATA and others - to join the startup as Chief Operating Officer.

"It's not every day your lead investor climbs into the trenches with you," said PINATA's CEO, Ian Ferguson. "This move is a testament to Rob's passion for data-driven SaaS, to M13's remarkable team of investors who are operators at heart, and to PINATA's massive opportunity to revolutionize real-world work."

Olson is an accomplished data scientist who founded the Data team at DigitalOcean (NYSE:DOCN) prior to joining M13. With expertise in scaling high-growth SaaS businesses honed as both operator and investor, he joins PINATA during a period of rapid organic adoption.

In the last year alone, PINATA has amassed over 5 million user-sourced data points and images across 20 thousand consumer products and 40 thousand storefronts. This growing dataset is driven by actionable "TaskFlows," enabling customers to orchestrate diverse field activities while establishing a crucial contextual throughline between planning, execution, and outcomes.

The strategic decision for Olson to join PINATA full-time is rooted in the company's long-term opportunity to leverage this extensive data to feed its product-led growth engine. "We've invested deeply in an underlying data architecture that is extensible, use-case agnostic, and perfectly suited to enhancement via AI," he said. "By developing this proprietary structure for our first-party data capture, we now have a connective tissue between more subjective, language-based data like the description of a product line's shelf placement, and all of the subsequent action-based data including follow-up assignments and restocking ordes. We have the foundation in place for an incredibly powerful Large Action Model, and we believe this type of AI agent-assisted workflow will drive incredible value for our customers."

The necessary fuel for this AI-enhanced product is a customer base that is organically expanding its platform usage - and thus data creation - in quantity, diversity and complexity. "This last chapter has been all about honing product-market fit in service of a land-and-expand commercial strategy," said Ferguson. "We've focused on delivering software that our customers want to use more and more, and we have the metrics that prove it." Those metrics include best-in-class net revenue retention, a 5x growth in average active users per organization since 2021, and a 10x "Flywheel Quotient" - the average number of external companies that each paying customer invites onto PINATA for collaboration around scheduling, third-party-staffing, field reporting, billing, and more. "The product foundation is there," Ferguson concluded. "So the next chapter is all about scaling the business in a way that is operationally efficient, while leveraging that scale to bring these AI capabilities to market - and that's why Rob is such an exciting and critical addition to our team."

Olson will be succeeded on the board of directors by Karl Alomar, Managing Partner at M13. Alomar will join Marc Ferrentino, former President and COO of Yext; Mike Morini, former CEO and current Board Member of WorkForce Software; Aaron Rudenstine, CEO of ButterflyMX; Ann Lai representing Bullpen Capital; and PINATA's co-founder Josh Wand, CEO of ForceBrands.

The company also welcomed another industry veteran making the move to PINATA, with Sam Anderson leaving his post as VP of Commercial Excellence at Breakthru Beverage Group to lead business development in PINATA's beverage alcohol vertical.


PINATA is the TaskFlow platform revolutionizing real-world work. Leveraging purpose-built TaskFlows, PINATA helps distributed teams orchestrate and optimize on-the-ground activity, delivering operational efficiency and invaluable performance insights - a dual impact on ROI.

PINATA serves as the single source-of-truth for real-world execution, bridging the gap between the C-suite and front-line operations. The platform acts as a hub to facilitate essential business processes such as invoicing and payments, and integrates seamlessly with other mission-critical systems like Anaplan.

Many of PINATA's customers focus on sales, marketing, and logistics activities in the field, and today include manufacturers, like E & J Gallo Winery; distributors, like Republic National Distributing Company; and retailers, like Amazon Fresh.

Headquartered in New York, NY, PINATA powers real-world jobs across all 50 states, connecting a multi-stakeholder ecosystem from local businesses and freelancers to regional hubs and national offices. For more information, visit

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