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/

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

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/

We're flipping the script - today's episode has Darren Mitchell interviewing the CEO/Co-Founder of Warmly - Max Greenwald - on The Exceptional Sales Leader Podcast. Tune in to learn the journey of the Revenue Rebels host!

Areya Dargahi leads mid-market sales at Gainsight, a Series E SaaS company that helps businesses drive efficient growth by unifying the post-sales customer journey. Areya has built out their mid-market sales team from scratch, and now his team is bringing just shy of $10 million ARR.

Gainsight started off as an enterprise-only solution and then moved down to target SMB and mid-market clients. They saw that smaller companies had outgrown the tools available to them and realized there’s a huge opportunity to expand.

Although from a product perspective there weren’t many strong competitors that rivaled Gainsight, their downmarket motion still required quite a bit of competitive intel and strategy to ensure that Gainsight wins those competitive deals.ls. What really helped them was setting up a slack channel where the whole team monitors their competitors and shares their insights - whether they are positioning changes, new content releases or notes from going head to head on a deal.

Areya is a huge proponent of quick response times during the sales process. While features do matter, for upmarket deals there’s always a possibility that a feature gets custom built for that client, but in order to build enough mutual trust for such a big, two-sided commitment, something as simple as quick response times can work wonders when putting prospects at ease during the sales process.

Tune into the full episode to learn why you should improve your sales process by taking a customer success approach!

HIGHLIGHTS:

0:00 Intro

2:44 Getting to Sales and Customer Success alignment
3:57 Moving from Enterprise to Mid-Market/SMB
5:13 Building Gainsights competitive intelligence
7:40 The importance of quick response times
11:01 Relationship vs Outcome selling
12:53 Winning the deal is only half of the battle
17:54 Account Executives need product expertise
22:31 How to approach teaching AE’s product

Connect with Areya - https://www.linkedin.com/in/areyad/

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

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

Steve Wright leads mid-market sales at Synergis, where they help companies find and retain top talent in technology. After 25 years of primarily serving enterprise clients, Synergis saw an opportunity to expand into mid-market - and the results have been phenomenal.

The magic of mid-market is that it allows you to work directly with decision makers who have strategic, tactical and contract signing abilities all in one. They have less established buying processes, which can be a huge relief if your company doesn’t yet have a fully fleshed out enterprise motion.

In today's softer market, mid-market companies are still big because they don't have the internal resources to do everything in-house. While enterprise clients can often leverage existing teams, mid-market needs external support to drive transformation. This has led to Synergis's mid-market division hitting 107% of plan even as enterprise slows.

For companies looking to expand into mid-market, success requires deep domain expertise and the ability to be advisory rather than just a silver-tongued seller. The best salespeople combine enterprise best practices with consultative selling skills while continuously working on their output metrics.

Tune into the full episode to learn how to build and scale a successful mid-market motion!

HIGHLIGHTS:
0:00 Intro
1:00 Why mid-market?
3:12 Rewriting the enterprise playbook
8:08 Mid-market vs enterprise in 2024
10:31 Should you start selling into the mid-market?
16:33 Small vendors winning big deals
21:10 Best AI tools in 2024

Connect with Steve - https://www.linkedin.com/in/stevenwwright/

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

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

Ali Schwanke (Founder @ Simple Strat) is an expert in helping companies get better and faster results through mastering HubSpot. Her company is a Diamond Solutions Partner and she’s the host of HubSpot Hacks, the #1 unofficial YouTube channel for HubSpot Tutorials.

Even though HubSpot positions itself as a plug and play solution that’s easy to set up, Ali believes that the best HubSpot strategies start with a whiteboard and a chart. You need an understanding of what exactly is the purpose of your CRM and how it can best integrate with your team's existing workflows.

Intent mapping has proven to be a winning tactic in 2024. With the right tech stack you can start to truly focus your sales efforts towards leads that have the highest likelihood of closing. Ali recommends identifying false signals like existing customer website visits to help make the process more efficient. Automations are a necessity, but over-automating can cause complications down the line, especially as you scale your team.

Tune into the full episode to get a real lesson in RevOps and master your CRM!

HIGHLIGHTS:
0:00 Intro
1:51 Product-market fit is a must
3:41 Clearbit + HubSpot = Data Enrichment
5:31 How to build better workflows on HubSpot
7:08 Orchestrations in HubSpot
9:11 First steps towards lead scoring
11:50 Lead Gen vs Demand Gen
13:21 HubSpot configuration dream state
16:11 Best HubSpot Hacks
19:17 There is no automation silver bullet
20:52 Top 5 Don’t Do’s in HubSpot
22:37 Max’s bonus Don’t Do
25:05 Top 3 HubSpot Dashboards

Connect with Ali - https://www.linkedin.com/in/alischwanke/

Connect with Alan - https://www.linkedin.com/in/alan-j-zhao/

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

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

Mike Lander is an expert at handling procurement and helping sales teams increase their win rates in the mid-market and beyond.

After years of founding companies, running consultancies and scaling teams, Mike took his experience as a buyer and started Piscari to help sellers better understand how buyers think and how to walk away from negotiations with their desired outcomes achieved.

The biggest mistake a seller can make when dealing with procurement is sticking their head in the sand and expecting the deal to go through. There’s a common myth that procurement refuses to work with SME’s - and that is simply not the case, as they value the flexible and entrepreneurial approach that smaller companies bring. To win over procurement, you need to understand what they value and be proactive with your approach.

One thing to always remember is that procurement aren’t the budget holders - they are the guardians of the budget, which means that their interests are aligned with mitigating risk and increasing savings. The best thing you can do is involve them early on - get added to their supplier lists, pass any checks and really introduce yourself so that you’re not starting over when the sales cycle looks to be almost finished.

Tune into the full episode to learn how to handle procurement and win upmarket deals!

HIGHLIGHTS:
0:00 Intro
3:04 Who are procurement teams and what do they want?
9:51 How to prepare for procurement
13:20 How to quantify ROI
15:49 Challenge procurements thinking
20:36 Who does procurement report to?
23:04 Stop wasting time on unwinnable deals
25:55 The Incumbent wins most of the time
27:27 Winning in competitive bid processes
30:04 Get good at RFP’s

Connect with Mike - https://www.linkedin.com/in/mikelander/

Connect with Alan - https://www.linkedin.com/in/alan-j-zhao/

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

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