James Stone (Head of Mid-Market Sales at HubSpot) has been with the company for 14 years, taking part in their growth from $30 Million ARR to $2.5 Billion in 2024. During this time, James has secured Presidents Club 9 times.

HubSpot’s brand is best known for their inbound sales motion. Today in the mid-market sector, James mentions that 25% of their pipeline comes from their business development org, 25-30% comes from their reps proactively prospecting, and another 40-50% comes from inbound and their partner org. The partner program has been a huge focus in recent years, as having HubSpot be part of the onboarding and success process really helps mitigate churn.

Tune into the full episode to hear more on how HubSpot is currently approaching their sales engine!

HIGHLIGHTS:

0:00 Intro
3:21 How HubSpot onboards 10+ new sellers per month
4:41 Identifying which reps will succeed
6:43 Where does HubSpot generate pipeline?
8:21 How customer expectations have grown
11:51 Get your prospects team involved
17:18 How the role of data is changing
19:57 Reigniting closed lost deals
22:01 Uncovering the champion for change
24:54 Tips on making Presidents Club

Connect with James - https://www.linkedin.com/in/jamesmstone/

Connect with Max - https://www.linkedin.com/in/max-greenwald/

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JD Miller (CRO, Operating Advisor, Author of The CRO's Guide to Winning in Private Equity) joined the show to help CRO’s beat the odds and stay in their roles longer than the average tenure of only 18 months.

So why exactly are CRO’s getting booted so early in their journey with a new company? The easy answer would be that they aren’t hitting their revenue targets - but JD doesn’t agree. During his time as a CRO and now being on the boards of multiple companies, JD has realized that the real issue lies in board communication and realistic forecasting. The lesson here is that CRO’s need to be transparent with the board and they absolutely cannot afford to avoid giving bad news. The CRO’s who show the board what the weather's going to be are the ones who will last in their roles.

JD’s experience as a CRO has shown him that the problem that organizations think they have isn’t always the reality. When he interviewed the company he joined, they were certain it was a sales issue, but after looking at the data - they were winning 35% of their deals, so the real issue at hand was lead generation. He doubled down on that and drove exceptional outcomes in the first 90 days.

Tune into the full episode to learn how to become a CRO that lasts!

HIGHLIGHTS:
3:11 Tips on going from $3 - $10 Million
4:36 Top performers aren’t always the best leaders
6:48 Is the sales compensation model outdated?
10:45 What skills should sellers prioritize in 2025?
14:41 Why is the average CRO tenure so low?
16:45 Diagnosing the real revenue problem
18:29 What makes a good CRO?
19:55 “Watch one, do one, teach one”
22:15 When should founders step out of sales?
24:31 Learning how to let go accelerates growth
27:47 Become a better CRO in 2025

Connect with JD - https://www.linkedin.com/in/jdmillerphd/

Connect with Max - https://www.linkedin.com/in/max-greenwald/

Want to convert your website visitors instantly? Try Warmly for free - https://warmly.ai/

Today’s episode welcomes Kris Rudeegraap, Co-founder and Co-CEO of Sendoso, the leading Sending Platform,that helps companies stand out by giving them new ways to engage with customers throughout the buyer’s journey.

A big part of Sendoso’s success is the fact that Kris built a platform based on his own domain expertise in sales. Back in 2014, he was an individual contributor who implemented strategic gifting as part of his sales strategy. He noticed exceptional outcomes tied to a very manual process and thought of building a better way.

Fast forward 8+ years, Sendoso is a staple brand in the B2B tech space with 400+ employees, $152 Million Dollars secured in venture capital and no signs of stopping. Tune into the full episode to hear Kris’ journey!

HIGHLIGHTS:

0:00 Intro

2:39 The Strategic Gifting method
4:43 How Kris came up with Sendoso
6:25 The journey of building Sendoso
10:15 How to transition out of founder-led sales
14:32 Should you implement strategic gifting?
20:04 Lead scoring matters
23:52 You need to use all available channels

Connect with Kris - https://www.linkedin.com/in/rudeegraap/

Connect with Max - https://www.linkedin.com/in/max-greenwald/

Want to convert your website visitors instantly? Try Warmly for free - https://warmly.ai/