I am joined by Blakely Graham, who is a board advisor to Left Main REI, host of the Not All Business Podcast, Founder and former CEO of TaskRay⁠. This one was a long time coming. On a personal note, my time at TaskRay was some of my most formative. I found a balance while there between my previous experience of excellence with true work life balance and a focus on values that stays with me. I am so grateful that Blakely and team took a chance in hiring me for a role that I was almost kind of qualified for and her friendship since then.

I'll do my best to summarize this episode, but it's more than worth a listen because I don't have enough characters to summarize it all.

Blakely's Salesforce journey starts in 2001 and spans a ton of roles and experiences. We dig deep into her experience founding TaskRay 15 years ago in 2010 as Bracket Labs as one of the early ISVs on the AppExchange where VCs told her that her business was not investable and it was "a lifestyle business" at best because the Salesforce ecosystem was too small. She grew it in spite of that and by the time they sold the business, they were getting endless inbound interest.

We talk about culture and values and why they were so important to her and the team at TaskRay. One of the core values was Connection that was the inspiration for Project Connection where the founders and I went to 5 cities and sat across the table from over 20 customers without an agenda outside of learning how our customers used the app. It drove focus for years to come that had nearly endless valuable outcomes like clarity of product roadmap, dramatically reduced churn, drove brand/marketing strategy, and much more.

She shares how founder conflict snuck up on her with Eric Wu as well as how they (eventually) resolved it.

As we switched gears to talk about gtm, Blakely shares how TaskRay evolved from the primary source of leads being the AppExchange with mostly SMB customers to more enterprise selling with content strategies, partnership motions, events, and more knobs we turned. The lesson is you are going to try stuff - some will work, some won't but you have to innovate and measure.

We talk about how to select and what you can expect from an advisor. At TaskRay, we rolled an advisor program out modeled after a talk Blakely listened to from Andy Wilson, founder of Logikcull. Shoutout to Phil Stern who was my sales leader advisor at TaskRay who helped me avoid many mistakes.

Show notes:

• Jolene Chan's LinkedIn where she was talking about a personal board of directors: https://www.linkedin.com/in/jolenec/
• Not All Business podcast with Heather Cooper: https://www.linkedin.com/company/not-all-business/
• Podcast with Andy Wilson from Logikcull where he discusses his advisor program that we modeled TaskRay's after: it starts at 14:05 and lasts 4 minutes  starts at 14:05 and lasts 4 minutes -https://podcasts.apple.com/us/podcast/saastr-236-logikcull-ceo-andy-wilson-on-%240-to-%2410m/id1089973241?i=1000439148009

This episode is brought to you by ⁠⁠⁠Invisory⁠⁠⁠. Invisory is designed to meet you where you are: in your cloud marketplace journey through a strong go-to-market strategy that helps drive prospect and co-sell opportunities with Salesforce, AWS, Microsoft, and Google.