The Digital Agency Growth Podcast

As summer winds down, many agencies face the same problem: pipelines that dried up in July and August, and a mad dash to generate momentum before year-end. In this episode, Dan lays out a practical action plan for September outreach — how to reset your business development, stand out to brands, and build the right conversations that lead to Q4 results.This is from Dan’s conversation with Stephen Woessner on the Sell With Authority podcast.what you’ll learn:Why most agencies waste energy chasing the tiny slice of prospects “ready to buy now” — and what to do instead.How to build trust with brands early, before they’re even in buying mode.Why cold outreach often fails in today’s noisy market, and how to shift your approach.The real scarce resource in business developmentHow to open doors with brands in a way that feels natural, not forced.Links & Resources:Sell With Authority Podcast

In this conversation, Roger Nairn, CEO of JAR Podcast Solutions, shares his journey from hobbyist to leading a top agency working with brands like Amazon and Lululemon. He discusses the importance of taking action over overplanning and reveals how a critical hire transformed his business. Roger highlights the need for creative sales strategies and emphasizes selling solutions to business challenges rather than just podcasts. He also dives into effective outreach tactics and building scalable systems that drive real results for clients.

Dan Englander, CEO of Sales Schema, specializes in helping marketing agency owners build their firms. He discusses the challenges agencies face in sales, emphasizing the dangers of relying solely on hope and referrals. Englander explains the importance of developing structured sales systems and the need to convert networks into reliable pipelines. He also highlights the significance of trust in today's sales dynamics and provides insights on mastering inbound and outbound marketing strategies effectively. His approach promotes genuine relationships over cold outreach for sustainable growth.

 In this episode, I sat down with Kristen Sweeney, the founder of Every Little Word — a boutique content and communications agency that’s laser-focused on helping complex B2B orgs share what they actually know in ways that actually work. We got into the nitty-gritty of what it means to build trust with subject matter experts, why most B2B content is fundamentally broken, and how Kristen made a huge decision to walk away from a partner that was 60% of her business. Timestamps00:00 – Intro & Kristen’s background01:03 – From Broadway to freelance writing03:03 – Business triples during COVID04:48 – Treating execs like peers, not titles06:22 – Sales copy and horizontal vs vertical relationships07:39 – Why so much outreach reads as either bragging or begging08:09 – Creating content that matches your ICP’s level09:47 – Executives can smell uncertainty11:49 – Emotions in B2B aren’t optional14:17 – Leaving a 60% revenue partnership16:24 – Selling to enterprise life sciences17:07 – Building trust through intros and relationships19:33 – Owning both sides: product and sales21:56 – The writing on the wall after 10KSB24:45 – Kristen’s Colby profile and systems for sales25:50 – Why process builds confidence in sales28:07 – Trust recession and the power of a real convo31:43 – Why life sciences felt like home35:25 – Balancing delivery with marketing38:18 – Doubling down on strengths with Substack40:00 – What Kristen’s excited about next🔑 Some Key TakeawaysKristen Sweeney walked away from a partner driving 60% of her revenue (on purpose), “Executives can smell fear” — and Kristen shares what actually earns their respectLinks & Resources:Website: everylittleword.coRelationship Sales at Scale™

In this week´s episode Stewart Gandolf joins me to talk through what it actually takes to niche down, build a sustainable agency, and scale without losing your sanity or soul. Stewart’s been in the healthcare marketing game for over two decades, and his experience building Healthcare Success into one of the top firms in the space is loaded with tactical insight.We talk about the trap of project-based work, how to structure your agency around recurring revenue, and why most agencies screw up their first few sales hires.🕒 Timestamps & Topics00:00 — How Stewart got his start and why he doubled down on healthcare03:15 — Direct mail, seminars, and the early version of inbound06:40 — NLP and the psychology behind language that converts11:20 — What drove their early growth (hint: it wasn’t salespeople)13:40 — Why project work is a trap and how to transition to retainers16:00 — Right-sized clients vs. resource-sucking whales18:20 — Inbound vs. outbound: nets, spears, and the bullseye metaphor21:20 — Stewart’s playbook if he were starting from scratch today25:00 — Authority assets: reports, seminars, and content that build trust29:10 — The daisy metaphor and avoiding entrepreneurial distraction31:45 — What most agencies get wrong with their first sales hire37:10 — Traits of a great agency salesperson (and why most don’t have them)40:00 — When to stop being your own best salesperson44:15 — Strategic partnerships and the next wave of AI opportunity47:45 — Final thoughts on staying relevant when the cheese movesA few things we covered.Most agency salespeople fail, not because they’re bad, but because there’s no clear positioning to sell.Links & Resources:🔗 Links & ResourcesHealthcare Success — Stewart’s agencyRelationship Sales at Scale™

Explore the transformative groundwork needed for agency growth as we approach 2025. Learn how to transition from freelancer to enterprise-level with a focus on specialization and strategic planning. Discover why adopting a fresh perspective is key in today's market and how ethical marketing can pave the way for sustainable practices. Embrace innovative client relationship strategies and the power of personalized outreach. Finally, find out how automating lead generation through effective follow-ups can give agency owners more freedom to grow.

Most agencies never crack eight figures. Mark Orttung helped one grow to $130M—by breaking every "safe" rule.In this episode, we dive into what agency owners at the $1–5M mark can actually do to punch past the common growth ceilings.The most important shift?He stopped selling to job titles—and started selling to buyers with something to prove.⏱ Timestamps00:00 – Intro: Why agencies need a rethink00:36 – Mark’s background: Accenture, startups, bill.com, Nexient02:23 – Studying AI in the 90s: symbolic vs neural nets04:30 – Stepping into Nexient at $39M—and losing $5M first06:59 – Early differentiation struggles and customer perception08:29 – Building product-style squads inside a services business10:38 – The big leap: shifting from selling people to selling outcomes11:08 – Simplifying the pitch: “life’s too short for crappy software”13:12 – Saying no to revenue: the scary path to focus14:14 – Selling without data: enterprise outbound as testing lab16:26 – Creating their own conference as a positioning feedback loop19:34 – Cross-industry client base: healthcare to gas utilities to tech20:25 – Specializing by service vs vertical in today’s world24:52 – Growth “walls”: from founder-led to decentralized structure29:21 – Change agents: how to spot internal buyers who take risks32:40 – The next wall at 150M and why he chose to exit36:56 – Getting ghosted on a term sheet, then driving a bidding war40:17 – The Project Works origin story: from spreadsheet to SaaS42:28 – Why every services firm needs better resourcing visibility47:29 – What’s next: proposal automation, AI, and growth tooling48:49 – Where to find Mark and Project WorksKey PointsWhy scaling past the eight figures in a services firm requires breaking the founder bottleneckWhy “life’s too short for crappy software” became a high-converting missionThe opportunity of building or early adopters—not the mainstreamHow to identify and win over internal change agents in large enterprisesHow Project Works helps agencies resource smarter and prevent margin leaksUsing conferences as real-time feedback loops for positioningWhy now is the time to apply AI to services growth ops—especially proposalsLinks & Resources:🔗 Links & Resources🔗 Book a strategy call with Dan: https://salesschema.com/work-with-us/🎙 More episodes of the Digital Agency Growth Podcast: salesschema.com/podcastProject Works – https://www.projectworks.comConnect with Mark on LinkedIn – Mark Orttung

In this episode of the Digital Agency Growth podcast, I’m joined once again by agency advisor Karl Sakas. Karl breaks down the philosophy and practice behind his new book Calm the Chaos—a leadership guide for agency owners who want to scale smart, delegate more, and reclaim time. We also explore his writing process, the parallels between art collecting and running an agency, and how to think clearly when chaos hits your business.⏱️ Timestamps00:00 – Welcome back Karl Sakas + Intro to Calm the Chaos01:09 – Why leadership is the key to scaling a lifestyle agency02:22 – Karl’s writing process05:30 – Blog posts vs. books: Why books matter for positioning07:45 – AI’s role in writing and idea development08:31 – Art collecting vs. agency leadership: Taste vs. discernment13:32 – The tipping point: You can’t be the answer person forever16:13 – The bottleneck around delegation and how to fix it21:50 – What causes chaos in an agency?24:50 – Strong pipeline = better client filtering29:27 – How to delegate growth and not abdicate responsibility34:48 – Should you build demand gen internally or hire it out?37:21 – The M&A market and how to think about valuation and exit41:51 – The real drivers behind agency exits: Age, tuition, and burnout🔗 Book a strategy call with Dan: https://salesschema.com/work-with-us/🎙 More episodes of the Digital Agency Growth Podcast: salesschema.com/podcast🎁 Get a free chapter of Karl’s book: bit.ly/karl-dag

Today, I talk to Todd Gagne—tech founder, startup mentor, and the guy who accidentally dropped a viral bomb on Substack after a weekend rabbit hole about GLP-1 drugs. We talk about why these weight-loss medications might be as transformative as the air conditioner, what this means for advertising, and why the next few years could upend how we think about consumer behavior, even in B2B.⏱️ Timestamps[00:00] – Todd’s background and startup school origins[01:20] – How a Substack detour into GLP-1 changed everything[03:33] – What GLP-1 drugs do, how they work, and why they matter[05:28] – The "air conditioner moment" analogy and downstream societal effects[07:14] – Grocery, alcohol, and aviation: second-order impacts[10:04] – What fills the lifestyle gap?[11:46] – The hidden threat to advertising: fewer impulses, fewer clicks[13:52] – Are your most impulsive ad converters vanishing?[15:15] – Even B2B isn’t safe from this shift[17:22] – Safety data, supply constraints, and the future scale of adoption[19:25] – Could insurance companies lead the charge on GLP-1 coverage?[21:15] – Could 50% of ad strategies go obsolete?[22:23] – Where to follow Todd and dig deeper📢 Key Topics:GLP-1’s societal and psychological impactWhy this isn’t just about weight loss—it’s about impulse controlSecond- and third-order effects on brands, industries, and cultureHow marketing strategies may need to evolve in a post-GLP-1 worldLinks & Resources:Visit: https://salesschema.com/work-with-us/🔗 Learn more about Todd→ https://wildfirelabs.io/

Join Dan Englander and Jared Gibson, co-founder of Outworks, as they dive into the future of B2B marketing and explain why personal branding is the most powerful growth engine for CEOs and founders.Discover why cold outreach is no longer enough, how authentic LinkedIn content can drive long-term trust and authority, and how busy executives can make content creation part of their routine. Jared also shares hands-on tactics for leveraging video and interviews, working smarter with teams, and setting realistic goals for lead generation through personal brands.Timestamps00:00 – Intro & welcoming Jared 01:51 – Jared’s background & launching Outworks 06:43 – Why traditional outbound no longer works 12:46 – How content & algorithms have changed on LinkedIn 18:51 – The importance of knowing your Total Addressable Market 23:35 – Making content creation a lifestyle 29:49 – What ROI looks like on LinkedIn 33:50 – Getting clients comfortable on video 35:21 – Using client interviews for content 37:21 – Jared’s partner program and new service launchTagsLinks & Resources:Visit: https://salesschema.com🔗 Learn more about Jared→ https://www.outworks.io/