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

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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!

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.

Maheen Bari

A Client Manager at CanadianSME, Maheen adds a practical, hands-on perspective to the podcast. Her experience in conducting interviews, coordinating events, and collaborating with business experts provides valuable insights into the day-to-day realities of running a small business. Her involvement in the magazine’s marketing initiatives also brings a valuable understanding of audience engagement and content strategy.

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