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Guest: Matthew Clare
LinkedIn: https://ca.linkedin.com/in/matthewjclare
Website: https://ujet.cx/
AI is changing customer service but automating more interactions doesn’t automatically mean better customer experiences or stronger business results.
In this episode of Scaling with People, host Gwenevere Crary sits down with Matthew Clare, VP of Product Marketing at UJET and a customer experience and contact center technology veteran, to explore how leaders can use AI to improve customer experience, make smarter workforce decisions, and uncover opportunities for growth.
Matthew explains why companies that rush to replace human support with AI can end up with frustrated customers, rising costs, and disappointing results. He shares practical examples of organizations using AI not just to automate routine work, but to reskill employees, expand into new markets, and identify the underlying problems that drive customer contacts in the first place.
In this episode, you’ll learn:
Matthew also demonstrates Spiral, UJET’s conversational analytics platform, showing how leaders can use natural-language prompts to analyze customer conversations, investigate staffing needs, identify churn drivers, and generate actionable recommendations.
The central takeaway: Don’t optimize only for fewer customer interactions. Optimize for fewer customer problems. When you understand why customers need help, you can fix the underlying issues, improve their experience, and free your team to focus on higher-value work.
If you’re a founder, executive, or business leader investing in AI, this episode will help you move beyond automation for automation’s sake and focus on measurable business outcomes.
About Matthew Claire
Matthew Claire is VP of Product Marketing at UJET. With 20 years of experience in customer experience, customer support, and contact center technology—including experience at Google—he helps organizations rethink how technology and human talent work together to deliver better customer experiences.
Explore Guide to HR: Visit guidetohr.com to learn how people strategy and AI-powered systems can help growing companies scale smarter.
Enjoyed the conversation? Share it with a leader navigating AI adoption, and subscribe to Scaling with People for more practical strategies to turn chaos into compounding growth.
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Guest: Sudeshna Sen
LinkedIn: https://www.linkedin.com/in/sudeshnasen
Website: https://joinpionyr.com/
What if the advice you’re following is actually slowing your business down?
In this episode of Scaling with People, host Gwenevere Crary sits down with Sudeshna Sen, serial entrepreneur, tech veteran, and founder of Pionyr, a network supporting women founders from pre-seed through Series B.
Drawing on her experience working with hundreds of founders, Sudeshna breaks down three common pieces of startup advice that can cost women entrepreneurs valuable time, money, equity, and opportunity. The problem isn’t always the advice itself—it’s following it without questioning whether it fits your business.
In this episode, you’ll learn:
- Why you don’t necessarily need a technical co-founder to get started. Explore how AI, no-code tools, fractional talent, and technical advisors can help you build and validate your idea. If you do bring on a co-founder, learn why you should test the working relationship, define roles and milestones, and establish clear equity terms before making a long-term commitment.
- How playing it too safe can limit your growth. Understand the difference between credible financial projections and underselling your vision, why underpricing can anchor customers to a lower value, and how to make a stronger case for your business without abandoning realistic assumptions.
- Why venture capital isn’t the only path to growth. Learn to think beyond VC and consider a capital strategy that fits your business, including customer revenue, grants, angel investors, and loans.
- How to evaluate advice without treating every opinion as a rule. Learn to look for patterns in feedback, ask why someone is making a recommendation, and use your own judgment rather than changing course based on a single investor’s perspective.
Sudeshna shares real-world examples of founders who rushed into co-founder agreements, struggled with missed milestones, and gave away equity before establishing whether the partnership would work.
Her central message: Investors don’t just fund co-founders—they fund progress. You don’t have to wait for the perfect partner, perfectly safe numbers, or a VC to say yes before moving your business forward.
If you’re a woman founder building your next big idea, this conversation will help you challenge conventional wisdom, make more deliberate decisions, and build leverage without waiting for permission.
About Sudeshna Sen
Sudeshna Sen is a serial entrepreneur and tech veteran with 20 years of corporate experience spanning sales, marketing, and data analytics. As the founder and CEO of Pionyr, she helps women founders access the support, expertise, and network they need to build and scale their businesses.
Connect with Guide to HR:
Visit https://guidetohr.com to learn how people strategy and AI-powered systems can help growing companies scale smarter.
If this episode helped you rethink a piece of advice, share it with a founder who needs to hear it, and subscribe to Scaling with People for more practical strategies for sustainable growth.
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Guest: Amanda Lannert
LinkedIn: https://www.linkedin.com/in/amandalannert
Website: https://www.jellyvision.com/
Do you really need a technical background, millions in venture capital, or a rapidly growing headcount to build a successful tech company?
Amanda Lannert, CEO of Jellyvision, challenges conventional startup wisdom. She helped transform a creative business into a profitable, privately held HR tech company known for Alex, its employee benefits platform used by more than 1,600 employers.
In this episode of Scaling with People, host Gwenevere Crary talks with Amanda about building a company around customer needs, growing profitably, and creating a culture where people can make decisions without everything running through the CEO.
In this episode, you'll learn:
Amanda's central message is simple: build a company around the value you create, not the conventional milestones you're expected to chase.
You don't have to follow someone else's startup playbook. You need to understand your customers, build a team that can solve meaningful problems, and create a business model that supports sustainable growth.
A question for founders: Are you measuring success by the money you've raised and the people you've hired—or by the value your business creates?
Subscribe to Scaling with People for practical conversations on leadership, people, and the systems that help growing companies scale smarter.
Learn more about Guide to HR at guidetohr.com.
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Guest: Maximos Lih
LinkedIn: https://www.linkedin.com/in/maximoslih
What happens when the skills that built your company become the very things preventing it from scaling?
In this episode of Scaling with People, Gwenevere Crary sits down with Maximos Lih, executive coach and founder of Embolden, whose experience recruiting engineering talent at Google and advising founders at Google Ventures gave him a front-row seat to hypergrowth companies like Uber, Slack, and Flatiron Health.
Maximos shares what the best founders do differently as their companies grow and why scaling isn't about doing more yourself. It's about knowing the difference between everything you can do and the things only you can do.
They explore:
One of the biggest takeaways: the culture that matters is the culture that exists when the founder isn't in the room.
As your company grows, your job isn't to approve every decision, solve every problem, or check every detail. Your job is to create the principles, people, and systems that allow great decisions to happen without you.
If you're a founder or business leader trying to scale without losing your culture, your people, or yourself in the process, this conversation is for you.
Key question to take away:
What are you doing today that someone else could do—and what are the things that only you can do?
Subscribe to Scaling with People for more conversations on leadership, people, AI, and the systems that help growing companies scale smarter.
Learn more about Guide2HR: guidetohr.com
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Revenue may look strong on paper—but if the cash isn't there when you need it, your business can still be in trouble.
In this episode of Scaling with People, host Gwenevere Crary sits down with Elaine Bogart, fractional CFO and financial leadership advisor, to demystify the numbers founders need to understand before scaling.
Together, they explore why revenue, profit, and cash are not the same thing and how a gap between making a sale and receiving payment can put pressure on payroll, operations, and business runway.
Elaine also explains how founders can use forecasting, AI, and the right financial leadership to make better decisions, avoid expensive surprises, and build a stronger financial foundation for growth.
In this episode, you'll learn:
Key takeaway
A strong sale is not the same as strong cash flow.
Founders need visibility into when cash will arrive, when expenses must be paid, and how much runway remains. A regularly updated cash forecast—combined with sound financial leadership—can help business owners make smarter decisions before a cash shortage becomes an emergency.
About Elaine Bogart
Elaine Bogart is a fractional CFO who works with founders, CEOs, and leadership teams across digital media, technology, creative agencies, professional services, and other industries. She helps businesses strengthen their financial systems, improve forecasting, prepare for growth, and make informed strategic decisions.
Chapters
00:00 — Welcome to Scaling with People
01:32 — Meet Elaine Bogart
02:28 — Turning finance into a strategic partner
04:13 — When spreadsheets and intuition stop working
06:03 — The cash gap between sales and payment
07:10 — Improving payment terms and cash flow
08:53 — How far ahead should founders forecast?
10:00 — Building a 13-week cash forecast
10:48 — The financial numbers founders should know
12:32 — AI forecasting and the need for human oversight
15:15 — AI workflows for forecasting and planning
17:45 — Using assumptions and asking better questions
18:28 — Comparing forecasts with actual results
19:22 — How forecasting can change business decisions
21:10 — Cash accounting versus GAAP accounting
24:22 — When should a company use GAAP?
25:44 — Choosing the right CFO for your stage
30:10 — Advisory versus embedded fractional CFO support
31:09 — The financial habit every founder should build
32:42 — Closing thoughts
Connect with Scaling with People
If this conversation helped you think differently about your company’s financial health, share it with another founder or business leader who needs better visibility into their numbers.
Scaling isn't just about speed. It's about people.
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Guest: Andrew Brooks
LinkedIn: https://www.linkedin.com/in/andrewcarrollbrooks/
Website: https://contextual.io/
AI is everywhere. But are you actually using it to build a competitive advantage—or just adding another chatbot to the business?
In this episode of Scaling with People, we sit down with Andrew Brooks, serial entrepreneur, multiple-time founder, and CEO of Contextual.io, to unpack what separates AI that genuinely transforms a business from AI that simply generates headlines.
Andrew has built and exited technology companies through multiple technology cycles. His perspective on AI is simple but powerful: don't think of AI as just another piece of technology. Think about how it can enable your people, transform your processes, and create new ways to serve customers.
We dig into what founders and business leaders should actually be thinking about before investing in AI—from measuring ROI and managing adoption to identifying the data, expertise, and customer relationships that could become a true competitive moat.
In this episode, you'll learn:
The big takeaway
Don't start by asking, “What AI tool should we buy?” Start by asking, “What makes our business unique—and can AI make that advantage stronger?”
For Andrew, the distinction between buying and building comes down to whether the AI capability deepens your moat. If it's a commodity task, use an existing tool. If it can turn proprietary data, expertise, or customer relationships into something differentiated, that's where building your own AI capability can create strategic value.
About Andrew Brooks
Andrew Brooks is a serial entrepreneur and the founder and CEO of Contextual.io. His career has included building technology companies across multiple technology shifts, with a focus on applying new technology to underserved markets. Today, Contextual.io focuses on practical, human-centric applications of AI for lower and mid-market businesses.
Chapters
00:00 — Welcome to Scaling with People
01:01 — Meet Andrew Brooks and Contextual.io
03:10 — The handwritten note advantage
05:40 — Why AI is different from previous technology cycles
09:34 — The biggest AI mistakes leaders make
11:55 — Moving from AI automation to business transformation
13:54 — Flashy demos vs. production reality
16:34 — The AI investment checklist that matters
20:54 — Designing AI as a real teammate
26:34 — Buy or build based on your moat
29:59 — The first 30 days start with data
31:36 — Turning internal and external data into insight
33:18 — Closing thoughts
Connect with Scaling with People:
If you found this conversation valuable, share it with a founder, CEO, or business leader who is trying to figure out what AI actually means for their company.
Scaling isn't just about speed. It's about people.
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How do you scale a business without losing control of quality, culture, or accountability?
Brad Coleman knows the problem firsthand.
A former NASCAR driver and longtime entrepreneur, Brad bought the driving school where he learned to drive and helped turn it into a growing franchise system. Today, Safeway Driving has expanded across multiple locations while keeping its focus on the mission that started it all: safety first.
In this episode of Scaling with People, Brad shares the systems, leadership principles, and guardrails that helped him grow without sacrificing what made the business successful in the first place.
We talk about what founders need to build before they scale—and why growing faster isn't always the goal.
In this episode, you'll learn:
A key lesson for founders
You don't scale by making yourself responsible for more.
You scale by building systems that other people can execute—and giving capable people enough responsibility to use their strengths.
Brad's approach is simple: establish the non-negotiables, build the playbook, train people well, and then give them room to operate inside the guardrails.
Because scaling isn't just about adding locations, employees, or revenue.
It's about making sure the business can perform consistently without everything depending on the founder.
About Brad Coleman
Brad Coleman is the CEO of Safeway Driving, a Texas-based driving school and franchise business. A former NASCAR driver, Brad brings lessons from high-performance racing teams into business leadership, franchise operations, training, and organizational growth.
Chapters
00:00 — Welcome to Scaling with People
01:26 — From Safeway student to owner
03:05 — What NASCAR teaches us about team execution
06:25 — Why franchising fit the mission
08:14 — Building the playbook before scaling
10:57 — Why quality comes before growth
12:49 — When the founder becomes the bottleneck
15:36 — Creating guardrails for autonomy and consistency
18:37 — Choosing the right franchisees and instructors
20:38 — Looking back on the franchise decision
21:48 — What businesses should consider before franchising
23:07 — Safety first: the leadership lesson
25:20 — Closing thoughts and next steps
Listen, follow, and share
If you're building a company and trying to scale without losing the people, systems, and quality that made it successful, follow Scaling with People for weekly conversations with founders and experts who've been in the trenches.
If this episode gave you an idea you can use in your business, share it with another founder who is trying to scale without losing control.
Scaling with People is brought to you by Guide to HR—helping high-growth companies scale smart with people strategies and AI-powered systems.
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To celebrate the milestone 150th episode of Scaling with People, host Gwenevere Crary steps away from the standard interview format for a candid, executive-level conversation on the real business value of HR. Joined by long-time friend, mentor, and 25-year HR executive Trina White (Founder of Swift Arc Strategic), the two break down why treating HR as a cost center silently drains profits—and how transforming your people strategy drives compounding growth.
Key Takeaways
Featured Guests & Host
Timestamps
Resources & Links
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Guest: Grace Tabib
LinkedIn: https://www.linkedin.com/in/gracetabib/
Website: https://dupayme.com/
You closed the deal. You delivered the work. So why isn't the money in your bank account?
In this episode of Scaling with People, Gwendaver Crury sits down with attorney and founder Grace Sabine to unpack one of the most overlooked threats to business growth: unpaid invoices.
Grace shares why getting paid isn't an administrative problem—it's a scaling, cash-flow, and founder-time problem.
Together, they explore:
The big takeaway: Getting the deal is exciting. Getting paid is what keeps the business alive.
If you're a founder, freelancer, agency, or business owner who has ever thought, “I'll just chase this invoice myself,” this conversation will make you rethink the true cost of that decision.
About Grace Sabine
Grace Sabine is a Columbia Law graduate and founder focused on helping businesses protect the revenue they've already earned. Through Dupe, she combines technology, AI, and human advocacy to help businesses recover unpaid invoices and build better systems around contracts and payments.
Listen now—and ask yourself: Are you actually growing if your revenue isn't reaching your bank account?
If you found this episode valuable, follow Scaling with People and share it with a founder who needs to hear it.
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Guest: Nick Avaria
LinkedIn: https://www.linkedin.com/in/nickavaria/
Website: https://agencyacquisitions.io
Your business can have a great strategy, strong leaders, and talented people—and still hit a growth ceiling.
In this episode of Scaling with People, Nick Avaria explains why the missing middle—the layer between senior leadership and frontline employees—can quietly become the biggest bottleneck to growth.
Nick has built, bought, and sold seven agencies and scaled multiple businesses to seven and eight figures. He shares the hard lessons that taught him why simply promoting high-performing individual contributors into management often fails—and what founders can do instead.
We dig into the difference between leadership and management, why high performers can become ineffective managers, and how unclear accountability and decision-making authority can cost a business real revenue.
Nick also breaks down a practical framework founders can use to create a management layer that actually scales.
In this episode, we discuss:
The four systems Nick recommends
1. Objectives, Metrics & KPIs
Give every role a small number of clearly defined objectives, measurable outcomes, and leading indicators.
2. Dashboards
Make performance visible so people can see what is happening and respond before problems become crises.
3. RACI / Permission Sets
Clarify who can make which decisions, what requires approval, and where each person's authority begins and ends.
4. Management Training
Teach managers how to delegate, manage performance, lead change, create accountability, and develop their people.
One question for founders
If you're constantly doing your managers' jobs for them, don't immediately assume you have the wrong managers.
Ask:
Did I actually give them the systems, authority, expectations, data, and training they need to succeed?
Because you don't scale a business by simply adding more people.
You scale the people who run it.
About Nick Avaria
Nick Avaria is a serial entrepreneur who has built, acquired, and sold multiple agencies and scaled businesses to seven and eight figures. His experience spans industrial services, consulting, digital marketing, agencies, and several unconventional businesses. His work focuses on the systems, management practices, and operating structures that help businesses scale more predictably.
About Scaling with People
Scaling with People is the weekly playbook for turning chaos into compounding growth. We go under the hood with founders and battle-tested experts across people, leadership, sales, marketing, operations, finance, and technology to uncover the systems and strategies that help businesses scale without breaking.
If this episode gave you a new way to think about your management layer, follow Scaling with People and share this episode with a founder who is trying to break through their next growth ceiling.
Learn more about Guide to HR at Guide2HR.com.
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