#4 — Gayle Charach (Global Head of Sales Enablement) From Camp Counsellor to Sales Leader

Gayle is a Sales Enablement leader with a demonstrated record of success and extensive experience driving cross-functional collaboration, customer and partner engagement and loyalty, and revenue and market share by empowering sales teams with the right coaching, tools and training to maximize productivity. When she is not working, she is a loving daughter, wife and mother trying to live her best life while caring for those in her life who mean the most.


Host, Paul Syng:

Guest, Gayle Charach:


Spotify, Apple, Anchor & more:


(00:00) How Gayle and I met

(02:08) Gayle’s current role as Global Head of Sales Enablement at vArmour

(03:34) From Winnipeg to Toronto

(07:07) Teamwork, collaboration, and other lessons learned from camp

(11:02) Driving results with the STAR methodology

(13:54) Trip to Israel and emotional regulation as a leadership skill

(19:20) Speaking in Eighth grade language for domain experts

(23:33) Not fitting into a box and Gayle’s car buying story

(32:52) Leading with story to invite people into the conversation

(38:38) Helping logical minds tell emotion-led stories

(43:06) From strategy to initiatives, change management and the role of collaboration

(52:16) Improving communication bandwidth between people and teams

(01:03:25) Building trust and bringing people on the journey by knowing what drives them

(01:10:13) Culture and behaviour as a result of incentive structures

(01:15:23) Connecting the people at the bottom with the top

(01:22:43) How Gayle got into sales

(01:28:08) Imposter syndrome, limiting beliefs and trusting yourself

(01:33:14) Advice for women looking for a career in sales

(01:40:06) Paul’s summary and learnings

(01:42:58) 3001 Questions all about me

(01:45:23) Closing remarks