Practical AI Strategies for B2B Sellers and Sales Leaders with Jason Tsai | MySalesDay

Description

AI has moved past the “is this real?” phase—and entered the “who’s actually adopting it well?” phase. In this episode of the My Sales Day podcast, Michael Hess sits down with Jason Tsai (joining from London) to break down what AI is actually doing inside modern sales orgs, where teams are still stuck, and how B2B sellers can use AI to sell more—not just produce more “work.”

Jason shares the career path that led him from media planning to digital transformation roles, and ultimately into AI enablement at Pivotal, a growth studio that doesn’t stop at strategy decks—Pivotal embeds with teams to implement change and drive adoption.

From there, the conversation gets practical:

Why AI tools are mature, but adoption is uneven
How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment
How AI helps verticalize value propositions without breaking brand governance
Where AI is useful for role-play, objection handling, and pressure-testing messaging
The difference between using AI to produce “work slop” vs. using AI to sharpen performance
Why the transformation is only half tools—and mostly human motivation, training, and habits

If you’re a seller, manager, or sales leader trying to figure out what to do next—this is a grounded, non-hype roadmap for using AI to reclaim selling time and raise the bar on how you prepare, message, and execute.

Featuring: Jason Tsai
Host: Michael Hess, MySalesDay Podcast

Timestamps

00:18 Welcome + first MySalesDay episode of 2026
00:40 Jason joins from London: “neither sunny nor dry”
01:23 The mission: tangible AI action items for sellers and leaders
02:10 Jason’s career arc: agency → publisher → Visa → ad tech → AI
04:03 Falling down the AI rabbit hole + the “no time to learn AI” insight
05:49 What Pivotal does: operator-led growth studio, implementation not slides
06:02 Jason’s team: AI enablement, workflow mapping, “robots” that speed up real work
08:32 Agenda: state of AI, skills impacted, adoption resistance
11:04 Where AI is today: beyond experiments, now “uneven adoption”
12:09 Sales AI example: Gong and what call data reveals
13:35 The 30% problem: sellers spend too little time actually selling
15:27 Leveling up prospecting: from ChatGPT searches to scale tools
16:19 Scaling research + enrichment: Clay/Apollo-style workflows
18:05 AI and value proposition: customization at the account/segment level
21:37 Governance: using AI to grade/pressure-test messaging before it ships
25:01 Negotiation prep: scripts, simulations, and objection handling practice
30:28 In-meeting AI: awkward live, powerful for preparation and post-call learning
48:13 Adoption resistance: tools are half the equation—humans are the rest
49:30 How to drive adoption: make it role-specific + prove time savings
51:24 Close: better habits equal better selling

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course, to help you excel and perform at your peak abilities.

My goal is to make your time here educational, inspirational, and actionable. And yeah, entertaining too…sales doesn’t have to be boring! Selling is fun too, so let’s have some of that here as well.

You'll get skill ideas, action items, and hugs.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Description

From there, the conversation gets practical:

Why AI tools are mature, but adoption is uneven
How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment
How AI helps verticalize value propositions without breaking brand governance
Where AI is useful for role-play, objection handling, and pressure-testing messaging
The difference between using AI to produce “work slop” vs. using AI to sharpen performance
Why the transformation is only half tools—and mostly human motivation, training, and habits

Featuring: Jason Tsai
Host: Michael Hess, MySalesDay Podcast

Timestamps

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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Description

From there, the conversation gets practical:

Why AI tools are mature, but adoption is uneven
How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment
How AI helps verticalize value propositions without breaking brand governance
Where AI is useful for role-play, objection handling, and pressure-testing messaging
The difference between using AI to produce “work slop” vs. using AI to sharpen performance
Why the transformation is only half tools—and mostly human motivation, training, and habits

Featuring: Jason Tsai
Host: Michael Hess, MySalesDay Podcast

Timestamps

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Description

From there, the conversation gets practical:

Why AI tools are mature, but adoption is uneven
How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment
How AI helps verticalize value propositions without breaking brand governance
Where AI is useful for role-play, objection handling, and pressure-testing messaging
The difference between using AI to produce “work slop” vs. using AI to sharpen performance
Why the transformation is only half tools—and mostly human motivation, training, and habits

Featuring: Jason Tsai
Host: Michael Hess, MySalesDay Podcast

Timestamps

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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