Revenue Problem Solvers

Operationalize

Revenue Problem Solvers delivers candid conversations with top business & revenue leaders who've mastered the art of growth. Each episode uncovers real-world challenges, practical solutions, and proven strategies that drive measurable results. No fluff or theory—just actionable insights from those who've successfully navigated revenue roadblocks. Listen as industry veterans share their playbooks for breaking through plateaus, optimizing sales processes, & creating sustainable revenue engines. Turn your toughest business challenges into opportunities with insights you can implement immediately

  1. What Sales Enablement Actually Is (And Why You're Doing It Wrong)

    3 DAYS AGO

    What Sales Enablement Actually Is (And Why You're Doing It Wrong)

    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.

    49 min
  2. How to Build a Pipeline on LinkedIn Without Cold Calling | Natasha Walstra

    27 MAR

    How to Build a Pipeline on LinkedIn Without Cold Calling | Natasha Walstra

    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.

    46 min
  3. If You Have 20 Priorities, You Have None | Nate Littlewood

    20 MAR

    If You Have 20 Priorities, You Have None | Nate Littlewood

    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.

    46 min
  4. Don't Let the Humans Touch the Data: How to Deploy AI and Actually Prove It's Working | Justin Shriber, Territ

    13 MAR

    Don't Let the Humans Touch the Data: How to Deploy AI and Actually Prove It's Working | Justin Shriber, Territ

    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

    47 min
  5. Growing From $300K to $26M Without a VP of Sales | Ross Paquette, Maropost

    6 MAR

    Growing From $300K to $26M Without a VP of Sales | Ross Paquette, Maropost

    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

    50 min
  6. Change Management in the Age of AI. Leadership, Adaptability & Revenue Growth with Neil Weitzman

    27 FEB

    Change Management in the Age of AI. Leadership, Adaptability & Revenue Growth with Neil Weitzman

    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 ever05:30 – The two types of people inside every organization09:45 – Why AI is different (and why it’s not)13:40 – “Will” vs. “Skill”, the real career divider18:25 – The power of direct, honest leadership conversations23:10 – A story every leader needs to hear28:50 – How individual contributors should show up33:20 – Why some professionals won’t survive the AI shift38:10 – The one action you should take this week41:45 – 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.

    38 min
  7. SaaS Pricing Strategy: How to Stop Leaving Money on the Table With Roee Hartuv

    20 FEB

    SaaS Pricing Strategy: How to Stop Leaving Money on the Table With Roee Hartuv

    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

    50 min
  8. Why Most GTM Leaders Get TAM Wrong (And How to Fix It) with Dan Wardle, VP Sales at Spellbook

    13 FEB

    Why Most GTM Leaders Get TAM Wrong (And How to Fix It) with Dan Wardle, VP Sales at Spellbook

    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. — 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

    47 min
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About

Revenue Problem Solvers delivers candid conversations with top business & revenue leaders who've mastered the art of growth. Each episode uncovers real-world challenges, practical solutions, and proven strategies that drive measurable results. No fluff or theory—just actionable insights from those who've successfully navigated revenue roadblocks. Listen as industry veterans share their playbooks for breaking through plateaus, optimizing sales processes, & creating sustainable revenue engines. Turn your toughest business challenges into opportunities with insights you can implement immediately

Information

  • Creator
    Operationalize
  • Years Active
    2025 - 2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © Operationalize
  • Show Website
    Revenue Problem Solvers