CanadianSME Small Business Podcast

The Playbook is Done: How Independent Tech Leaders Win High-Stakes Deals

Episode Notes

Welcome to the CanadianSME Small Business Podcast, hosted by Maheen Bari. Today, we explore independent consulting, vendor-neutral technology strategy, and the keys to successfully leading digital transformation in mid-market organizations in 2026.

Joining us is Keith Daser, Founder and CEO of Deliver Digital, who shares insights on moving from corporate roles to independent consulting, avoiding first-year pitfalls, and ensuring digital projects succeed.

Key Highlights

1. Barriers to Independence: Keith explains why experienced tech leaders hesitate to become independent consultants.
2. Year-One Struggles: Keith highlights the common challenges new consultants face in their first year.
3. Collaborative Over Lone Wolf: Keith discusses why solo consulting models are no longer effective.
4. Vendor-Neutral Advice: Keith emphasizes the need for unbiased tech guidance in mid-market companies.
5. Avoiding Digital Project Failure: Keith shares strategies to prevent digital transformation projects from failing.

Special Thanks to Our Partners:

• UPS: https://solutions.ups.com/ca-beunstoppable.html?WT.mc_id=BUSMEWA
• ADP Canada: https://www.adp.ca/en.aspx

For more expert insights, visit www.canadiansme.ca and subscribe to the CanadianSME Small Business Magazine. Stay innovative, stay informed, and thrive in the digital age!

To learn more about how we are supporting the ecosystem, please visit the CanadianSME Small Business Foundation at smbfoundation.ca.

Disclaimer: The information shared in this podcast is for general informational purposes only and should not be considered as direct financial or business advice. Always consult with a qualified professional for advice specific to your situation.