Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Mark Kosoglow.

Mark graduated from Penn State University in 1998 and then became the General Manager of Nittany Notes where he was responsible for everything from hiring, training, development, inventory management, and of course, sales. After discovering his knack for sales Mark went on to hold two more long-term sales positions before finally landing himself the gig of a lifetime as the VP Sales for Outreach in 2014.

Mark is among the rare breed of VP Sales who held his position for over 8 years, including a promotion to SVP of Sales, prior to leaving Outreach. At which point he became the CRO of Catalyst Software in 2022, where he remained until February of this year when he started working on his most recent project Operator, where he now serves as Co-Founder & CEO.

Mark believes that as an industry we got greedy and wrecked the outbound model. The playbook was simple and worked, so we automated it and ignored how resistant buyers were becoming. After having lived through the brightest and darkest times of outbound sales in B2B SaaS, I can say I wholeheartedly agree and I’m darn curious to learn how Operator plans to address this problem.

Before we get started, if you’re watching on YouTube, please take a moment to subscribe to the channel, like the video, and leave us a comment if you have questions. If you’re joining us from Spotify or Apple Podcasts, please drop us a review and let us know what you think of the episode. This stuff really helps to grow the audience.

Without further adieu, let’s dive in and find out more specifically what Mark thinks is broken with outbound and how he plans to fix it.

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TOPICS:

00:00:00 Intro

00:03:35 Outbound Sales is Broken

00:09:20 Growth-at-all-Costs

00:18:18 AI in Sales

00:25:30 Sales Quota Attainment

00:30:36 VP Sales Average Tenure

00:38:33 Raising a Salesperson

00:44:28 Operator

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QUESTIONS:

1. What’s broken with B2B outbound and how did we get here?

2. What’s happening to the Growth-at-all-Costs model?

3. What’s your take on AI in sales over the next 5-10 years?

4. What do you think is the reason for low sales quota attainment?

5. What do you think is the reason for low VP Sales average tenure?

6. What’s it like raising a second generation B2B SaaS salesperson?

7. How is Operator going to change the game?

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LINKS:

Operator: https://www.operator.ai

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Jeron Paul.

Jeron studied economics and philosophy at Brigham Young University and then received his MBA at Harvard. After school he spent 3 years as a consultant before starting his first company Boardlink, which was acquired by Thomas Reuters. Jeron then spent 5 years in venture capital before starting his next two companies Scalar and Capshare, both with successful exits.

With all of that experience behind him, in 2018 Jeron founded Spiff which was acquired by Salesforce in February of this year for $419 million. In episode 9 I spoke to Spiff’s Chief Marketing Officer, Anna Fisher and I sat on their GTM advisory board for 3 years until the acquisition.

Jeron believes every person has an infinite potential to do good and his goal in life is to unlock as much of that potential in himself and others as possible. He believes in fighting group think, the Socratic method, and the power of humility. One of the things he’s most proud of is sharing larger than normal equity stakes with those who are bold enough to build businesses with him, and I can say after having been an advisor on the receiving end of the Salesforce acquisition equity, he practices what he preaches in that regard and that’ll be one of the topics we’ll dive into today.

It’s been 7 months since Spiff was acquired. Since then, Jeron has served as the SVP of Product at Salesforce, presumably continuing to oversee Spiff, but without further adieu, let’s dive in and learn more about what it took to build Spiff and sell it to Salesforce in just 5 and a half years.

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TOPICS:

00:00:00 Intro

00:01:49 What is Spiff

00:07:39 GTM Advisory Board

00:16:01 Equity Philosophy

00:27:16 M&A

00:30:04 Growth Channels

00:37:40 Doing it again today

00:42:06 Who should use Spiff

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QUESTIONS:

1. What is Spiff and why did you build it?

2. You decided early on to build a GTM advisory board; what were your main motivations and goals behind doing this and was it worth it in hindsight?

3. We often hear stories of founders finding creative ways to screw people out of their equity at the time of acquisitions and IPOs, but you did the opposite. Talk me through your philosophy on equity and the decisions you had to make during the acquisition as it pertains to employees and advisors liquidating their shares.

4. Was M&A always the plan? Or did the pandemic and financial crisis play a role in the decision to sell?

5. What were your main growth channels and can you share roughly the split of revenue that came from each, like inbound, outbound, channel partners, etc.?

6. If you were to start Spiff today would you do anything different?

7. Is Spiff still a product for non-Salesforce users or is it now specifically for Salesforce users?

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LINKS:

Spiff: https://spiff.com

Jeron on X: https://twitter.com/jerondanielpaul 

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Chris Orlob.

Chris studied marketing at Utah Valley University and then went on to start his career at InsideSales.com, after which he started his own company Conversature, which eventually merged with Gong, at which point Chris became the Director of Product Marketing and eventually the Head of Sales where he helped grow the company from $200k ARR to over a $7B valuation in 5 years.

In 2022 Chris left Gong to start his current venture, where he serves as the Founder and CEO of Pclub.io, a sales training platform that aggregates courses from top practitioners into one platform.

The last time I spoke with Chris was back in 2019 and it feels like just about everything has changed since then with the advent of remote work, sales AI, and the divergence from the Growth-at-all-Cost model, so I’m excited to dive in and get his thoughts on all that’s changing.

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TOPICS:

00:00:00 Intro

00:02:12 Outbound Prospecting

00:11:37 Remote vs Office

00:16:42 Quota Attainment

00:23:48  Average Tenure

00:30:24 Growth-at-all-Costs

00:36:43 AI in Sales

00:41:20 Pclub

--

QUESTIONS:

1. Outbound prospecting has become increasingly challenging as conversion rates for calls and emails continue to decline. What do you think outbound salespeople should be doing differently today?

2. What’s the best way to build a sales team in 2024; remote, hybrid, or in the office, and why?

3. Average quota attainment is under 40%. Why do you think it’s so low and what needs to change?

4. Average VP Sales tenure is below 18 months. Why do you think it’s so low and what needs to change?

5. What’s happening to the Growth-at-all-Costs model?

6. What role do you see AI playing in sales over the next 5-10 years?

7. What is Pclub?

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LINKS:

Pclub: https://www.pclub.io

Chris on X: https://x.com/Chris_Orlob

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Stefan Katanic.

Stefan is a lifelong entrepreneur. He co-founded Traden Group in 2013, Coinbio in 2017, and White Label Agency in 2019, but his most recent venture is where he truly found his stride. Today Stefan serves as the CEO of Veza Digital, a services business that helps B2B SaaS companies build and operate profitable marketing websites that build awareness, trust, and credibility at scale.

They’ve quickly become the go-to website agency for B2B SaaS, having built websites for companies like ChiliPiper, Adonis, Trumpet, and Shipwell to name a few.

I talk a lot about SaaS on this podcast but have yet to talk about the services aspect of B2B, which is not only a massive percentage of the total sales world, but in this case is one of the services SaaS companies rely on heavily for growth.

With SaaS pivoting to remote operations, companies are now relying more on outside agencies to manage aspects of their business, like Sales Operations, Finance, HR, and website development, maintenance, and SEO.

Stefan has been running founder-led sales for Veza Digital for the past 8 years and is now ready to shift his focus toward mergers and acquisitions and needs to prepare the company for bringing in an external sales leader, which I’ll be helping him with as a Consultant over the coming months.

In the meantime, my audience is mostly made up of salespeople, many of which hope to start their own companies someday. Since most salespeople don’t know how to write code, starting a services business is often the more realistic option, so, I’m excited to dive in and find out how you found your niche and what it takes to build a multi-million dollar B2B services agency.

--

TOPICS:

00:00:00 Intro

00:03:19 Starting Veza Digital

00:05:16 Your elevator pitch

00:09:05 Targeting B2B SaaS

00:16:04 Your sales experience

00:20:58 Your sales process

00:24:41 Founder-led sales transition

00:28:58 Hiring a sales team

00:35:09 Starting a services business

00:41:42 Mergers and acquisitions

00:42:37 Number one sales objection

00:47:56 Why choose Veza Digital

00:51:59 Advice for young entrepreneurs

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QUESTIONS:

1. What led you to starting Veza Digital?

2. What’s your elevator pitch for Veza Digital?

3. How did you decide to focus on the B2B SaaS niche?

4. How much sales experience did you have prior to starting Veza Digital?

5. What has been the key to perfecting your sales process?

6. After 8 years of founder-led sales, why is now the time to add a sales team?

7. You’ve tried a few times to hire and train salespeople, why hasn’t it worked?

8. What’s the blueprint for starting a services business?

9. Why are mergers and acquisitions part of your growth strategy?

10. What’s the number one objection you face in your sales process?

11. What’s the main reason customers choose Veza Digital over competitors?

12. What’s one piece of advice you have for young salespeople who want to start their own company?

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LINKS:

Veza Digital: https://www.vezadigital.com

Veza Digital on X: https://x.com/VezaDigital

Stefan on X: https://x.com/stefan_katanic

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Yuriy Zaremba.

Yuriy is a corporate lawyer turned CEO and a 2x Y Combinator Alumni. He co-founded his first company AxDraft in 2017 which was acquired by Onit in 2020. He then co-founded AiSDR where he serves today as the CEO.

AiSDR creates and sends personalized sales emails at scale and automatically engages with prospects who respond. Tools like AiSDR spark a lot of conversation today because on one hand they have the potential to make outbound prospecting significantly more cost efficient, but on the other hand there’s concern about what that means for the future of sales jobs and the human seller.

In previous episodes we’ve discussed the future of AI in sales and have speculated our thoughts on what’s to come, but today we get to hear first-hand from the man who’s actually building and selling this solution, and I’m excited to get his perspective.

--

TOPICS:

00:00:00 Intro

00:01:24 AI taking human jobs

00:08:21 AI capabilities

00:19:47 Open and reply rates

00:28:11 Revenue and customers

00:31:19 Your sales process

00:37:39 Greatest obstacle today

00:39:00 AiSDR competitors

00:41:21 Y Combinator

00:45:00 Who should use AiSDR

00:46:53 The future of AiSDR

--

QUESTIONS:

1. People are concerned about the potential of AI taking away human jobs. What are your thoughts on this topic?

2. What is AI actually capable of today and 5-10 years out?

3. What are the average open and reply rates for AiSDR today?

4. Can you tell us how much revenue you’re at today or how many paying customers you have?

5. How do you sell it? Do people try it for free and it sells itself? Or do they have to pay to try?

6. What is the main focus at AiSDR today? Is there one thing that’s holding you back?

7. Who are the real competitors and how is AiSDR different?

8. How helpful is Y Combinator?

9. Who should use AiSDR today and who shouldn’t?

10. What does the future look like for AiSDR?

--

LINKS:

AiSDR: https://aisdr.com/

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Howard Lerman.

Howard went to Duke University where he founded his first company with two of his classmates, JustATip.com, which they sold for $150,000 in 2001 while still in college. After school Howard founded Yext in 2006. By 2016 the company had $89 million in revenue and in 2017 it was listed on the New York Stock Exchange. In 2022 Howard stepped away as CEO of Yext in order to focus on his newest project, Roam, where he serves today as the Founder and CEO.

This is the first time I’m speaking with Howard, but I’ve known of him since my very first sales job in 2012 at SinglePlatform since we sold competitively against Yext. Our companies even competed in Dodgeball and Basketball tournaments in NYC, so the competition was fierce but all in good fun. I’m excited to finally get acquainted.

In this episode, we react to a series of Howard's LinkedIn posts.

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TOPICS:

00:00:00 Intro

00:01:20 Best cultures are cults

00:10:30 Top salespeople

00:12:22 What you want VS Reality

00:16:19 Politics at work

00:22:38 Success and risk

00:30:07 Threat of OpenAI

00:31:20 Sales AI

00:38:12 Remote Work

00:41:15 Customer led growth

00:51:29 What is Roam?

--

QUESTIONS: (1-6 are from Howard’s Linkedin posts)

1. The best cultures are actually a cult, and that is the foundation upon which greatness begins.

2. I’d take a top seller at a medium company over a medium seller at a top company any day.

3. There will always be an annoying gap between what you want the world to be and how it actually is. Knowing when to stand your ground or when to be flexible is one of the most important growth skills you can learn.

4. The most successful people I know didn’t work the hardest. They took the most risk.

5. Founders, I would be very, very, careful about launching an AI startup right now. Unless you have something extremely special and you know exactly what you’re doing. The overwhelming odds are you will be buzz-sawed by OpenAI.

6. Too many companies make the mistake of forcing unnaturally fast growth right now at the expense of compound growth later on.

7. What is Roam?

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LINKS:

Roam: https://ro.am/

Howard on X: https://x.com/howard

Collin on X: https://x.com/collincadmus

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Jacco van der Kooij.

Jacco is originally from the Netherlands. He started his career in 1994 at Philips Electronics as a Project Manager and then transitioned into sales. Since then he’s led sales for over 10 different companies, prior to starting his current company, Winning By Design, where they help B2B SaaS Companies design, build, and scale their sales efforts.

Jacco’s voice in sales is respected globally as an author, keynote speaker, and all across social media. I’ve been following his content for as long as I’ve been in sales (if you’re not, you should be too). I could easily talk to him for weeks without running out of topics or questions, but today we’re going to focus on one specific topic that Jacco believes to be the number one issue facing SaaS companies today; and that’s the declining efficiency of go-to-market performance.

In the last 3 episodes we talked a lot about this subject, so it’s close to my heart. To keep things simple I’ve divided the episode into 4 questions, and I’m excited to dive in.

--

TOPICS:

00:00:00 Intro

00:01:56 What’s Growth-at-all-Costs / GaaC?

00:05:06 What’s broken with GaaC?

00:21:57 What needs to change?

00:41:32 Will GaaC return?

--

QUESTIONS:

1. What is the growth-at-all-costs (or GaaC) model?

2. What (if anything) is broken with the GaaC model and why is now the time for change?

3. What needs to change?

4. Will there be a return of GaaC when money is cheap again?

--

LINKS:

Winning By Design: https://winningbydesign.com/

Revenue Architecture Hardcover: https://a.co/d/2gUFzXx

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Hello and welcome back to the Collin Cadmus Podcast. Today I’m joined by Kevin Dorsey.

Kevin went to the University of Wisconsin-Madison and started his sales career where he quickly rose from entry-level selling to high-ranking leadership roles at SnackNation, ServiceTitan, PatientPop, and Bench Accounting.

He’s built sales teams from 0 to 150 reps and scaled revenue north of $100M ARR. Kevin believes in focusing on the person in salesperson and he shares his sales wisdom across social media, speaking engagements, podcasts, and most recently through the creation of his new online course the Sales Leadership Accelerator.

Kevin serves as an advisor to top startups around the world, he’s the host of the Live Better Sell Better Podcast, and he’s become a prominent voice in the B2B sales community. It’s been a while since we last collaborated, so I’m excited to catch up and dive into 5 very important topics.

--

TOPICS:

00:00:00 Intro

00:02:31 Average quota attainment

00:17:58 Average tenure of VP Sales

00:31:30 Growth at all costs / VC model

00:45:32 The impact of AI in sales

01:04:28 Sales Leadership Accelerator

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QUESTIONS:

1. The average quota attainment in B2B SaaS is under 40%. Why do you think it’s so low and what needs to change?

2. The average tenure for a VP Sales in B2B SaaS is under 18 months. Why do you think it’s so low and what needs to change?

3. What are your thoughts on the "growth at all costs" mindset / VC model?

4. What are your thoughts on AI and how it’s impacting sales today and going forward?

5. What is the Sales Leadership Accelerator?

--

LINKS:

Sales Leadership Accelerator: https://www.salesleadershipaccelerator.com/

Live Better Sell Better Podcast: https://podcasts.apple.com/us/podcast/a-candid-conversation-with-collin-cadmus/id1518419694?i=1000528139008

Modern Outbound System: https://www.collincadmus.com/the-modern-outbound-system

Sales Coaching: https://www.collincadmus.com/sales-coaching

Founder Coaching: https://www.collincadmus.com/founder-coaching

Collin Cadmus Podcast: https://www.collincadmus.com/podcasts/collin-cadmus-podcast

Revenue Growth Blog: https://www.collincadmus.com/blog

--

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

It's safe to say the average salesperson in 2023 is significantly better than the average salesperson of 10 years ago, yet the average quota attainment continues to decline.

This is the result of an inflationary economic system that drove competitive recruitment efforts toward the promise of higher OTEs, which inevitably led to higher quotas, which eventually far outpaced any salesperson's ability to keep up.

This means the "valuation narrative game" ultimately resulted in over-stressing talented salespeople to the point of exhaustion and an illusion of failure which was often actually stellar performance. In this episode I dive into how the quota system became what it is today (broken) and what needs to be done to fix it.

There's work to do on both sides; salespeople knowing how to vet employers and employers knowing how to incentivize salespeople for optimized results. Strategy is best left for folks managing the front-lines, not the folks balancing the spreadsheets.

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.

Welcome back to the pod! In this first episode I take a short break from my usual personality of bubbly positivity to begin this new season on a serious note and set the pace for what's to come.

The world has changed, the economy has changed, Silicon Valley has changed, and B2B SaaS has changed forever. Decades of mistakes have led to where we're at but valuable lessons are here to be learned.

I'm voicing these sentiments because they need to be said, need not to be forgotten, and need to be the foundation upon which we learn and rebuild the B2B SaaS industry into something bigger, better, and more honorable than ever before.

Sit back, relax, enjoy the episode, and thank you for listening, viewing, and subscribing.

Available on: YouTube, Rumble, Spotify, and Apple Podcasts.