Radical Scale: Go-to-Market Strategy for Uncertain Times

By Parasvil Patel

Radical Scale is a regular feature that explores key strategies for growing early stage technology companies.

Over the past several months the Radical Impact Team has hosted expert roundtables with our portfolio companies. We’re now sharing the key strategic and tactical insights from those sessions. Previous features include:  

This issue of Radical Scale looks at how to evolve your go-to-market strategies and plans while keeping your team engaged and motivated in face of uncertainty. Thank you to Greg Sybersma, Sarah Ryerson, and Seann Gardiner for sharing their insights.

Key strategic takeaway

The best way to deal with uncertainty is to constantly iterate over the course of brief go-to-market experiments with the goal of identifying winning strategies and tactics for broader implementation. To run successful experiments, keep them short (10-12 weeks or shorter), communicate regularly to share learnings within the team, and define metrics to measure success.

While the insights mentioned here are relevant for dealing with the uncertainty caused by COVID-19, they are equally relevant for startups confronting uncertainty due to changes in their strategy (pivots), environment (competitor entries and acquisitions), and markets (new geography or sector expansion).

Tactical advice


  • Rethink sales processes to navigate near term turmoil and prepare the organization for an eventual return to (new?) normalcy
    • Follow an iterative process to understand market dynamics and generate data to drive long term changes
    • If in-person meetings must be scaled back (as experienced during the pandemic), allocate more resources to a lower-cost inside sales team vs. outside sales teams
    • Implement a new incentive structure that balances activities that will lead to short term (<12 months) as well as medium (24-36 months) revenue


  • Identify leading indicators that can serve as a trigger for developing a replan for targets and activities
    • Monitor indicators such as movement through the pipeline and changes in close rates in addition to the usual impact measures such as new customers added, bookings, etc. 
    • If possible, track customer engagement with the product to identify sectors and customer types that are likely to respond favorably in the near term


  • We are living through extraordinarily uncertain times – it is important for sales leaders to show genuine empathy for their team and for the sales team to show empathy with the customers they are engaging with
  • Build a culture which emphasizes the notion of ‘shared pain and shared gain’
    • Celebrate successes and include cross-functional teams in those celebrations
    • Communicate team focus repeatedly, proactively, and across levels
    • Invest savings from reduced travel spend in activities such as training or tools that will enable the team for future success


  • Use this opportunity to explore new technology platforms that increase efficiency in the entire GTM process
    • Leverage automation capabilities offered by sales enablement tools such as Outreach, SalesLoft, or Mixmax
    • Explore conversational marketing platforms such as Qualified, Intercom, and Drift to engage with potential customers and understand what messaging resonates
    • Use tools that make it easy to standardize, cross reference, and enrich data (e.g. People.ai, Crossbeam, and LeanData)
  • Continue focusing on driving process discipline to gain full advantage of these new tools


Greg Sybersma is a Go-To-Market Strategist who partners with CEOs & executive teams to reinvigorate and scale their business. For 15+ years, Greg worked with global leaders, including Bearing Point, Blackboard, and Ancile, to restructure and grow direct and channel organizations, launch new products into new industry verticals and revive lagging solutions. These days, Greg works with high-potential startups to build-out their GTM capabilities, including Crypto-Numerics, a data-privacy startup recently acquired by Snowflake. Greg has an engineering degree from the U. of Waterloo and an MBA from the U. of Western Ontario.

Sarah Ryerson is President of TMX Datalinx, responsible for leading the growth of TMX Datalinx, the information services division of TMX Group which provides a broad spectrum of real-time and historical data solutions to clients around the world. Before joining TMX, Sarah served as Head of Industry, Financial Services at Google. In this role, she was responsible for driving revenue growth and innovation in the Canadian banking and insurance sector. Prior to Google, Sarah designed and implemented business strategies for private and public sector clients across a wide range of industries while at McKinsey & Company.

Seann Gardiner is currently SVP of Business Development at ThoughtSpot. Seann has close to two decades of extensive experience in the BD space. Prior to ThoughtSpot, he led business development at DataRobot and Alteryx. He has also held senior BD roles at Dell and Sophos. Seann has an MBA from Queen’s University and is a graduate of Royal Roads University.


About the Radical Ventures Impact Team

The Radical Ventures Impact Team is dedicated to helping its portfolio companies achieve global scale by providing deep technology expertise, go-to-market guidance, talent acquisition, strategic communications, and policy support.

If you want to learn more about Radical or its GTM impact efforts, please reach out to Parasvil Patel at parasvil@radical.vc.

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