Revenue Problem Solvers

Your enablement team is a dumping ground.

Every department pushes change into the sales org and calls it enablement. No sequencing. No cascading. No intake. The "just send it to them, they'll figure it out" mentality does NOT work!Because they won't.

Andrew Quinn spent over a decade at HubSpot executing the playbook behind The Sales Acceleration Formula; except he was the one who actually had to make it work. He scaled HubSpot's sales enablement organization to a global team of 40 people and ran over 500 discrete enablement initiatives in a single year. All of them landed.

In this episode of the Revenue Problem Solvers Podcast, Andrew breaks down why enablement is a business discipline, not a department, how to build an intake process that protects your sales team from change fatigue, and the three things every enablement leader should do before building another piece of content.

If you lead a sales team, run enablement, or are building your GTM function for the first time, this one will change how you operate.

Sponsored by Virtual Causeway.

Stop chasing form fills and start showing up where buyers already are. Visit virtualcauseway.com and mention the show for a special rate.

Most sales professionals know LinkedIn matters. Very few know how to make it work.

Natasha Walstra spent a decade figuring out the difference, starting as an SDR who could not stomach cold calling car dealerships, discovering that connecting on LinkedIn before calling changed everything, and eventually training sales teams and building a framework she now calls the REALationship Growth Method.

In this conversation, she breaks down what separates people who get pipeline from LinkedIn from the ones who get ignored.

You will hear why your LinkedIn profile is likely costing you deals before you ever reach out, how to think about content as trust infrastructure rather than an audience play, and the exact sequence she uses to warm a cold contact into a ready conversation over time.

There is also a stat that should change how you think about LinkedIn opportunity: 1.2 billion users, less than 1% posting original content. If you are willing to show up like a human, the space is less competitive than you think.

This episode is sponsored by Virtual Causeway. If your demand gen isn't converting, they help revenue teams get found by buyers who are already looking. Visit virtualcauseway.com and mention the show for a special rate.

If you have 20 priorities, you actually have none.

That's the first thing Nate Littlewood tells founders when they come to him overwhelmed, overworked, and wondering why their revenue growth isn't showing up in the bank account.

Nate is a fractional CFO who took an unusual path to get here. He started on Wall Street as a top-ranked equity analyst, trained to tell the story the numbers actually say. Then he went and built something himself, co-founding Urban Leaf and bootstrapping a sustainable e-commerce brand from Kickstarter to seven figures.

Now he helps e-commerce and consumer packaged goods founders get profitable, get clear on their numbers, and identify the 2 or 3 things that will actually move the needle, instead of spinning on a list of 30.

In this conversation, Nate breaks down how he built his fractional CFO practice by niching down across three layers: role, stage, and vertical. He shares why most founders launching a consulting business waste time on websites and logos before they have a single client. And he names the financial blind spot that quietly kills founder-led businesses even when revenue is growing.

This is a practical, honest conversation about building a services business, getting profitable as a product company, and using financial clarity as a real competitive advantage.

This episode is sponsored by Virtual Causeway. They help revenue teams shift from chasing leads to showing up where buyers are already searching. Check them out at virtualcauseway.com and mention the show for a special rate.

Want more from Nate? Find him at futurereadycfo.com or connect with him on LinkedIn. He also hosts his own show, Profits On Purpose, where he breaks down the financial side of building a profitable business. Worth adding to your queue.

Most AI revenue projects fail before they start. The technology is not the problem. The data underneath it is.

Justin Shriber is the co-founder and CEO of Territ and a former VP at LinkedIn who has spent 25 years inside some of the most complex revenue organizations in tech, including Oracle and McKinsey. In this episode he breaks down the exact three-stage framework CROs should follow to deploy AI, measure real ROI, and grow revenue without simply adding headcount.

He walks through the real math: what it actually costs to hit 25% growth the old way versus the AI-driven way. The numbers will change how you think about your next hiring plan.

What you will take away from this conversation: why dirty CRM data kills AI projects before they launch, the three leading indicators that tell you AI is working before revenue moves, why the average rep only touches 60% of their accounts and what to do about it, and how to build a business case for AI investment that holds up in a boardroom.

This one is for CROs, founders, RevOps leaders, and anyone responsible for making AI pay off in a B2B sales org.

Revenue Problem Solvers Podcast is sponsored by Virtual Causeway.

#RevenueProblemSolversPodcast

Ross Paquette built Maropost into a global commerce and marketing platform over 13 years. No venture capital. No VP of Sales for longer than most founders would be comfortable admitting.

In this episode, Ross breaks down exactly how he built a revenue engine from scratch when he had no choice but to own it himself. He talks about the $30M ceiling he hit as a founder, the $8M in failed expansion attempts across Toronto and Chicago, and why most bootstrap founders make the same hiring mistakes over and over.

This is not a highlight reel. It is a real conversation about what it actually takes to go from startup to scale when you are running lean and every wrong hire sets you back months.

What you will hear in this episode:

Why founder-led sales drove explosive growth from $300K to $26M in under 30 months. The real cost of hiring before your system is ready. How Ross finally figured out his own ceiling as a founder and what he did about it. The shift from startup dictator to scale-up CEO and why that transition is harder than it sounds. Why he stopped selling candidates on the company and started filtering for the ones who could actually handle the reality. Three things every founder should do before posting that VP-level job.

If you are building a bootstrap business and trying to figure out how to grow revenue without unlimited runway, this episode was made for you.

Ross Paquette is the founder and CEO of Maropost. Find him on LinkedIn - https://www.linkedin.com/in/rossandrew1/ - or at maropost.com.

The Revenue Problem Solvers Podcast is hosted by Karl Ortmanns. New episodes drop weekly for founders, revenue leaders, and operators who are serious about building.

Sponsored by Virtual Causeway. Learn more at virtualcauseway.com.

#RevenueProblemSolversPodcast

Entrepreneurship, Sales, Business, SaaS, Marketing, Startups, Leadership, Management

AI isn’t just changing tools. It’s changing leadership.

In this episode of Revenue Problem Solvers, I sit down with fractional CRO and GTM advisor Neil Weitzman to unpack what change management really looks like in today’s AI-driven world.

After 25+ years building revenue engines at Rogers Media, Nielsen, and Deloitte, Neil has seen every kind of transformation. But AI may be the ultimate leadership test.

This conversation covers:

02:10 – Why change management feels harder than ever
05:30 – The two types of people inside every organization
09:45 – Why AI is different (and why it’s not)
13:40 – “Will” vs. “Skill”, the real career divider
18:25 – The power of direct, honest leadership conversations
23:10 – A story every leader needs to hear
28:50 – How individual contributors should show up
33:20 – Why some professionals won’t survive the AI shift
38:10 – The one action you should take this week
41:45 – Where to connect with Neil

If you’re a founder, CRO, sales leader, or revenue operator trying to navigate constant change, this episode will challenge how you think about growth, mindset, and leadership.

Because AI isn’t replacing leaders.

But it is exposing them.

Neil is a fractional CRO and GTM advisor who partners with founder-led B2B SaaS and technology companies to deliver speed, clarity, and zero drama. He is also a long-time Pavilion ambassador and works closely with consultants and fractional executives through the CAF community.

Connect with Neil:LinkedIn - https://www.linkedin.com/in/neilweitzman/
Linktree - https://linktr.ee/neilweitzman

This episode is sponsored by Virtual Causeway.

Traditional demand generation is breaking. Virtual Causeway helps revenue teams shift from demand generation to demand positioning, engineering where and how your brand appears when buyers research through AI tools and peer networks.

Learn more at virtualcauseway.com. Mention the show for a special rate.

Pricing and packaging is the single most important growth lever in your business, and the one most leaders are afraid to touch.

In this episode of Revenue Problem Solvers, I sit down with Roee Hartuv, Senior Pricing Advisor at WillingnessToPay.com, who has spent two decades seeing how growth breaks when pricing doesn't reflect the value companies actually deliver.

The conversation covers everything:

- Why no one owns pricing until it's too late

- How to move from seat-based to usage-based models without disrupting your business

- The right way to validate a price increase with your most important customers

- Why packaging is more important than the number itself.

If you know you're leaving money on the table but don't know how to fix it; this episode is your starting point.

KEY INSIGHTS:

- Pricing touches every team: Product, Finance, Sales, CS, Ops. That's why it's so hard

- Most companies revisit pricing every 3–5 years. It should be every product cycle.

- Price the customer, not the product. The willingness to pay varies by segment

- Packaging is more important than the price point

- The validation process: internal → trusted customers → field test → roll out

- OpenAI changed their pricing 10 times in 12 months. If they're iterating, you should be too.

Guest: Roee Hartuv | LinkedIn: linkedin.com/in/roeehartuv | willingnesstopay.com

Sponsor: Virtual Causeway. Creating demand positioning for B2B revenue teams. virtualcauseway.com

#SaaS #PricingStrategy #B2BRevenue #RevenueProblemSolversPodcast #GoToMarket

Most companies define their Total Addressable Market incorrectly.

And it quietly limits their growth.

In this episode of the Revenue Problem Solvers Podcast, Dan Wardle, VP of Sales at Spellbook (AI legal tech serving eBay, Dropbox, and enterprise legal teams), breaks down why TAM is not a math exercise. It's a leadership decision that shapes retention, revenue, and long-term company value.

If you're selling to customers who won't retain, you're not growing. You're resetting the clock.

We talk about:

* The brutal truth about TAM vs ICP that most GTM leaders ignore

* Why retention matters more than short-term revenue

* When to narrow your market and when to expand it

* Product-market fit signals that actually matter

* The "two-person test" for smart market expansion

* How to hire sales teams without burning cash

* How they built a team where 100% hit quota

Dan shares real strategies from scaling legal tech in one of the fastest-moving AI markets.

Perfect for founders, CROs, VPs of Sales, and go-to-market leaders who want to scale intelligently and sustainably.

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This episode is brought to you by Virtual Causeway. As traditional demand generation gets noisier, Virtual Causeway helps B2B companies shift to demand positioning by engineering where and how your brand appears when buyers research. Visit VirtualCauseway.com and mention Revenue Problem Solvers for a special rate.

Connect with Dan: linkedin.com/in/wardledan

Most revenue leaders are obsessed with new leads. Meanwhile, they're sitting on hidden revenue in their existing customer base.

In this episode, Stephanie Valenti (SVP at BILL) shares how she built a post-sales motion that outperformed new business, all without hiring a single new rep.

You'll learn:

- Why your existing customers are your fastest path to growth

- The lions vs zebras framework for structuring revenue teams

- The childhood question that reveals if someone's in the wrong role

- How to build a post-sales motion in a transactional business

- The exact moment Stephanie realized post-sales could outperform new business

KEY TIMESTAMPS:

02:45 - Why CROs default to net new

07:30 - Lion vs Zebra sales teams

14:10 - The churn blind spot (months 3–9)

22:40 - The ONE post-sales metric that matters

31:15 - How to redesign quotas for net growth

41:00 - What new revenue leaders should do first

52:30 - Monday morning action steps

CONNECT WITH STEPHANIE:

LinkedIn: https://www.linkedin.com/in/stephanievalenti/

Thank you to the great team at Virtual Causeway for sponsoring this episode. To learn more, visit www.virtualcauseway.com and mention the show for a special rate.

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You hit your quarterly revenue target. Your team is underwater. Your capacity planning is broken. Sound familiar?

Simon Drexler, President of Samuel Automation, explains why booking cadence is the growth constraint nobody talks about. Getting $9M in bookings during the final month of a quarter looks identical to $3M per month on paper. Operationally, they're completely different businesses.

One creates predictability and sustainable growth. The other creates chaos, firefighting, and burned-out teams.

Simon brings a rare perspective: engineer turned revenue executive who has scaled industrial automation across automotive, medical devices, and consumer products for over a decade. He treats revenue operations like an engineering problem, which means he actually measures what works.

In this episode:

• Why inconsistent bookings kill your business heartbeat, even when you hit the number
• How lumpy revenue cascades into hiring mistakes, broken capacity plans, and lost focus on growth
• The validated learning loop that separates guessing from scaling
• When you actually have product-market fit (it's not what you think)
• Why turning off what doesn't work matters more than finding the next new thing
• What relentless customer behavior analysis looks like in practice

This episode is for you if:

• You're a revenue leader tired of hitting targets but feeling behind

• You're a founder trying to build predictable growth, not just chase bookings
• You're a CRO, VP of Sales, or RevOps professional questioning why growth feels harder than it should
• You're scaling a business and need frameworks that actually work in complex sales environments

About Simon Drexler:President at Samuel Automation. Former General Manager at ATS Automation Products Division. Former Product Line Lead at Clearpath Robotics (self-driving vehicles). Started as a project engineer and rose through program management to executive leadership. P.Eng., MBA. He has built automation systems on four continents and applies that systems thinking to revenue growth.

Sponsored by Virtual CausewayTraditional demand gen is breaking. Virtual Causeway helps revenue teams shift from demand creation to demand positioning. Instead of chasing form fills, they engineer where and how your brand appears when buyers are actively researching.

The result: fewer cold outreach motions, more high-intent conversations, and revenue teams spending time with people who actually want to buy. Learn more at virtualcauseway.com and mention the show for a special rate.

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Hosted by Karl Ortmanns