In this episode, I sat down with the Happy Clients Podcast to talk about what’s working in agency sales right now, without the cringe, without the outdated playbooks, and without turning you into a full-time cold caller.

Most agencies can sell for their clients all day, but when it comes to their growth, things can get messy.

I’ve spent the better part of a decade helping agencies stop relying on “hope and referrals” and start building sales systems that work.

⏱ Timestamps

00:00 – The “spare-time sales” trap

00:29 – Why this matters for client-facing pros

01:19 – My path into agency sales

02:20 – The scaling pain you don’t see coming

04:41 – When referrals run dry

06:10 – Inbound vs outbound today

07:04 – The trust-first approach

09:23 – Making referrals predictable

11:48 – Why cold outreach is harder now

14:13 – Accountability in sales

16:32 – Quick wins with clarity and focus

18:53 – Opportunities hiding in plain sight

20:10 – Where to find me + my book

✨ Key Points

• Why loading sales onto busy account managers fails.
• How to turn your network into a steady pipeline.
• The simple way to make introductions effortless.
• Why agencies should own sales instead of outsourcing it.
• How clarity on your ideal client changes everything.

🔗 Book a strategy call with Dan: Relationship Sales at Scale™

Checked the podcast on @dotandcompany

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.

Timestamps

00:00 – Intro & Kristen’s background

01:03 – From Broadway to freelance writing

03:03 – Business triples during COVID

04:48 – Treating execs like peers, not titles

06:22 – Sales copy and horizontal vs vertical relationships

07:39 – Why so much outreach reads as either bragging or begging

08:09 – Creating content that matches your ICP’s level

09:47 – Executives can smell uncertainty

11:49 – Emotions in B2B aren’t optional

14:17 – Leaving a 60% revenue partnership

16:24 – Selling to enterprise life sciences

17:07 – Building trust through intros and relationships

19:33 – Owning both sides: product and sales

21:56 – The writing on the wall after 10KSB

24:45 – Kristen’s Colby profile and systems for sales
25:50 – Why process builds confidence in sales

28:07 – Trust recession and the power of a real convo

31:43 – Why life sciences felt like home

35:25 – Balancing delivery with marketing

38:18 – Doubling down on strengths with Substack
40:00 – What Kristen’s excited about next

🔑 Some Key Takeaways

Kristen Sweeney walked away from a partner driving 60% of her revenue (on purpose), “Executives can smell fear” — and Kristen shares what actually earns their respect

Links & Resources:

Website: everylittleword.co

Relationship 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 & Topics

• 00:00 — How Stewart got his start and why he doubled down on healthcare
• 03:15 — Direct mail, seminars, and the early version of inbound
• 06:40 — NLP and the psychology behind language that converts
• 11:20 — What drove their early growth (hint: it wasn’t salespeople)
• 13:40 — Why project work is a trap and how to transition to retainers
• 16:00 — Right-sized clients vs. resource-sucking whales
• 18:20 — Inbound vs. outbound: nets, spears, and the bullseye metaphor
• 21:20 — Stewart’s playbook if he were starting from scratch today
• 25:00 — Authority assets: reports, seminars, and content that build trust
• 29:10 — The daisy metaphor and avoiding entrepreneurial distraction
• 31:45 — What most agencies get wrong with their first sales hire
• 37:10 — Traits of a great agency salesperson (and why most don’t have them)
• 40:00 — When to stop being your own best salesperson
• 44:15 — Strategic partnerships and the next wave of AI opportunity
• 47:45 — Final thoughts on staying relevant when the cheese moves

A 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 & Resources
• Healthcare Success — Stewart’s agency
• Relationship Sales at Scale™

This solo episode is a deep dive into the unsexy but transformative groundwork that agency owners need to lay to build a reliable new business engine. Dan breaks down what really separates enterprise-level agencies from the ones stuck in "Cobbler’s Children" limbo — not just in terms of tactics, but in mindset, strategy, people, and execution. He shares hard-won lessons from years of running Sales Schema and coaching 200+ agencies, including how to stop waiting for referrals, start building durable outbound systems, and shift from reactive selling to a process that actually compounds.

This is for the agency owner who's sick of feast-or-famine cycles and is ready to take control of their pipeline without chasing hacks or magical software.

⏱️ Timestamps

00:00 – The Rainforest vs. The Lion Hunt: A better metaphor for agency growth

02:00 – Introduction: Why solo episodes are the hardest, but the most needed

03:15 – The 4 Agency Growth Stages: Glorified Freelancer → Enterprise

06:00 – Specialization: Why it's now table stakes, not a nice-to-have

08:30 – TAM Thinking: Apply tech startup logic to your agency niche

10:00 – Why perspective is becoming table stakes

13:20 – You don't need to "go inward" for 6 months — talk to the market now

15:30 – Mindset: The difference between Cobbler’s Children and Enterprise thinking

20:00 – Why only 3% of your market is in-market right now.

24:00 – All marketing is interruption marketing — so do it ethically

26:00 – Why you probably don’t actually know your close rate (and how to fix that)

27:45 – Getting out of the sales seat: What really needs to be true before you hire a salesperson

30:30 – Your first two strategy projects: Thought leadership & net-new relationships

33:20 – The “balance beam” metaphor for doing outreach

35:00 – Using data + context to build non-spammy outbound lists

37:00 – What our best-performing campaigns look like

39:00 – Where real lead gen lives: Manual outreach to old prospects

42:00 – My exact reconnect email — word for word

44:00 – Wrapping up: Build something buyers want, but also build for your peace of mind

Key Points

• The Four Stages of Agency Growth
• → Glorified Freelancer → Cobbler’s Children → Transitional Agency → Enterprise
• Specialization is Now Table Stakes
• → It’s harder to win without it. But specialization doesn’t always mean verticalization.
• Perspective is the New Differentiator
• → Agencies that win aren’t just executing.
• 3% Rule of Market Timing
• → Only 3% of your market is actively buying.
• Manual Outreach is Still King
• → My highest ROI activity: emailing past prospects and lapsed clients.
• Getting Out of the Sales Seat Takes More Than Hiring a Salesperson
• → You need the wave. That means systems, clarity, and enough leads to support a new closer.

Links & Resources:

💼 Book a call with me

• Digital Agency Growth Podcast

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.

⏱ Timestamps

00:00 – Intro: Why agencies need a rethink

00:36 – Mark’s background: Accenture, startups, bill.com, Nexient

02:23 – Studying AI in the 90s: symbolic vs neural nets

04:30 – Stepping into Nexient at $39M—and losing $5M first

06:59 – Early differentiation struggles and customer perception

08:29 – Building product-style squads inside a services business

10:38 – The big leap: shifting from selling people to selling outcomes

11:08 – Simplifying the pitch: “life’s too short for crappy software”

13:12 – Saying no to revenue: the scary path to focus

14:14 – Selling without data: enterprise outbound as testing lab

16:26 – Creating their own conference as a positioning feedback loop

19:34 – Cross-industry client base: healthcare to gas utilities to tech

20:25 – Specializing by service vs vertical in today’s world

24:52 – Growth “walls”: from founder-led to decentralized structure

29:21 – Change agents: how to spot internal buyers who take risks

32:40 – The next wall at 150M and why he chose to exit

36:56 – Getting ghosted on a term sheet, then driving a bidding war

40:17 – The Project Works origin story: from spreadsheet to SaaS

42:28 – Why every services firm needs better resourcing visibility

47:29 – What’s next: proposal automation, AI, and growth tooling

48:49 – Where to find Mark and Project Works

Key Points

• Why scaling past the eight figures in a services firm requires breaking the founder bottleneck
• Why “life’s too short for crappy software” became a high-converting mission
• The opportunity of building or early adopters—not the mainstream
• How to identify and win over internal change agents in large enterprises
• How Project Works helps agencies resource smarter and prevent margin leaks
• Using conferences as real-time feedback loops for positioning
• Why now is the time to apply AI to services growth ops—especially proposals

Links & 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/podcast

• Project Works – https://www.projectworks.com
• Connect 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.

⏱️ Timestamps

• 00:00 – Welcome back Karl Sakas + Intro to Calm the Chaos
• 01:09 – Why leadership is the key to scaling a lifestyle agency
• 02:22 – Karl’s writing process
• 05:30 – Blog posts vs. books: Why books matter for positioning
• 07:45 – AI’s role in writing and idea development
• 08:31 – Art collecting vs. agency leadership: Taste vs. discernment
• 13:32 – The tipping point: You can’t be the answer person forever
• 16:13 – The bottleneck around delegation and how to fix it
• 21:50 – What causes chaos in an agency?
• 24:50 – Strong pipeline = better client filtering
• 29:27 – How to delegate growth and not abdicate responsibility
• 34:48 – Should you build demand gen internally or hire it out?
• 37:21 – The M&A market and how to think about valuation and exit
• 41:51 – 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

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.

Timestamps

00:00 – 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 launchTags

Links & Resources:

Visit: https://salesschema.com

🔗 Learn more about Jared→ https://www.outworks.io/