Her Path to Revenue

In this episode of Her Path to Revenue, Janelle sits down with Deidre Hudson, a growth-focused marketing executive and former CMO with more than 20 years of experience scaling FinTech, SaaS, and e-commerce companies.

Deidre has built her career around turning marketing from a collection of activities into a predictable revenue system. Her approach? Understand the inputs, define the process, operationalize what you can, and free your brain to focus on the work that actually requires creativity and strategic thinking.

But this conversation goes well beyond revenue strategy.

Deidre opens up about being in a reflective season of life, navigating major personal and professional changes, questioning what she wants next, and learning to challenge the thoughts and assumptions that have shaped her decisions. She shares how stepping back from the constant pressure to “do it all” ultimately helped her approach her next career move differently.

We also get into AI, but not in the usual “you better learn this or you’ll fall behind” conversation. Deidre shares how she’s using AI as a second brain and creative extension rather than handing over her thinking to it—and why keeping yourself in the driver's seat matters.

And, of course, we get personal. From her go-to confidence boost of Miley Cyrus's Flowers and ChatGPT to the advice she'd give her younger self about faith, forward momentum, and not waiting for perfect, this episode is about building a career and life that actually moves you forward.

In this episode, we cover:

• How to turn marketing into a more predictable, operationalized revenue system
• Why operationalizing the right things can free your brain for higher-value creative work
• The difference between the art and science of marketing
• What it means to be in a reflective season and intentionally question where you're headed
• How personal and professional transitions can change the way you approach your next move
• Why Deidre chose a mindset shift over simply “pounding the pavement” in her job search
• How to use AI as an extension of yourself instead of letting it do your thinking for you
• The AI tools Deidre is exploring and why she's having fun with them
• Why retention should be a priority when deciding between optimizing what you already do and building something new
• How to navigate the pressure to constantly keep up with AI and technology
• Deidre's go-to confidence boost: Miley Cyrus's Flowers and ChatGPT
• The role of faith in navigating uncertainty and major life transitions
• Why you don't have to wait for perfect—and how forward momentum creates more momentum
• The advice Deidre would give herself 10 years ago: believe it's going to be okay and keep moving forward

Follow Deidre on LinkedIn: https://www.linkedin.com/in/deidrehudson/

Deidre is also the author of How the Fuck Did I Get Here? A Candid Exploration of Identity, Power and Reinvention.

In this episode of Her Path to Revenue, Janelle sits down with Tamar Gill, bootstrapped founder, CEO, mom of four, and grandmother, to talk about what it really takes to build a successful company when you don’t have outside funding, a massive marketing budget, or a safety net.

Tamar’s journey has been built on hard work, resilience, and a commitment to doing exactly what she says she’s going to do.

Over six years, she has grown her company by focusing on something that can be easy to lose sight of in the race for growth: trust.

Her philosophy is simple: revenue built on trust lasts longer than revenue built on hype.

From being underestimated as a smaller, bootstrapped company competing against larger, VC-backed players to navigating cash flow, hiring, competition, and the pressure of wearing every hat in the business, Tamar shares the lessons she’s learned along the way and why she doesn’t believe you need to win everyone.

But this conversation goes beyond revenue and business strategy. Tamar and Janelle also get real about motherhood, entrepreneurship, confidence, being underestimated, and what it means to stop trying to fit into rooms that were never built for you.

In this episode, we cover:

• Why revenue built on trust lasts longer than revenue built on hype• The importance of setting realistic expectations and overdelivering• What happens when companies promise the world but fail to deliver• Why being bootstrapped can be both an advantage and a challenge• How to compete against larger, VC-backed companies without compromising your values• Why you don’t need to win everyone and how knowing when to walk away can protect your business• The real cost of “cheap” data and why cheap doesn’t always mean cost-effective• What it feels like to be underestimated and how Tamar responds to it• How she balances running a company while raising a family• Why Tamar believes in integrating work and life instead of chasing perfect work-life balance• Her go-to confidence boosters when she needs to remind herself, “You’ve got this”• The advice she would give herself 10 years ago: stop trying to fit into rooms that weren’t built for you and build your own

Follow Tamar on LinkedIn: https://www.linkedin.com/in/tamargill/

After a short break, I'm back bringing you exciting topics. After a four-month maternity leave, I’m officially back with Her Path to Revenue and I couldn’t be more excited to get back to the conversations I love.

In this quick comeback episode, I’m sharing a little about why I stepped away, what life looked like during my time off, and what you can expect from the podcast moving forward.

Thanks for hanging with me while I took a little break. Now, let’s get back to it!

In this episode of Her Path to Revenue, Janelle sits down with Summer Poletti. A revenue consultant, former corporate leader, and system-building strategist to unpack what it really takes to scale revenue without breaking your team, your pipeline, or yourself.

Summer’s journey didn’t follow a straight line. From navigating multiple functions across marketing, customer success, and sales to climbing the corporate ladder while raising her kids, she built her career through grit, adaptability, and a refusal to turn down opportunities to learn. Today, she brings that full-picture perspective to help companies fix what’s actually holding them back from growth.

But what stands out most isn’t just her experience—it’s her unapologetic focus on truth: most companies don’t have a pipeline problem… they have a system problem.

In this episode, we cover:
• Why most companies don’t have a pipeline problem—they have a system problem
• The biggest revenue killer: misalignment across marketing, sales, and customer success
• How to define what a “good lead” actually looks like (and why it matters)
• The real reason sales teams fail to convert—and how to fix it
• What founders get wrong when hiring their first salesperson
• When (and how) to build systems as you scale
• The role of accountability in eliminating team friction and finger-pointing
• Why sales is a foundational skill—regardless of your role
• The importance of building your personal brand before you need it
• Summer’s journey balancing motherhood, leadership, and entrepreneurship

Follow Summer on LinkedIn: https://www.linkedin.com/in/summer-poletti-rhymes-with-spaghetti-27207812/

Summer's Podcast Link References:

Increasing revenue without adding headcount:https://www.theriseofus.com/podcast/episode/1f5b3a41/6-strategies-to-increase-revenue-without-increasing-headcount

What to have in place before you ire:https://www.theriseofus.com/podcast/episode/1d8500f2/hiring-your-first-salesperson-part-2-how-to-avoid-an-expensive-lesson

In this episode of Her Path to Revenue, Janelle sits down with Alice Heiman—sales advisor, speaker, and self-proclaimed Chief Sales Energizer—to unpack what it really takes to build scalable revenue engines while sustaining your energy, health, and life outside of work.

Alice’s journey didn’t start in sales. From special education teacher to working alongside her father at Miller Hyman, to helping sell the company to private equity and eventually advising high-growth CEOs—her path is anything but traditional.

But what stands out most isn’t just her experience—it’s how she’s built a career rooted in longevity, discipline, and self-awareness.

From navigating burnout and chronic fatigue to designing a workweek that actually supports performance, Alice shares a deeply practical and honest look at what it takes to sustain success over decades—not just quarters.

If you’ve ever felt like building revenue comes at the expense of your well-being, this conversation will challenge that assumption.

In this episode, we cover:
• How Alice transitioned from teaching into enterprise sales and consulting
• What she learned from helping sell a company early in her career
• Why energy—not just strategy—is a sales leader’s greatest asset
• Practical ways to manage low energy, burnout, and even chronic fatigue
• The power of calendar discipline and structuring your week for success
• Why “balance” looks different for everyone—and how to find yours
• The importance of undivided attention in both work and family life
• How to build a business that supports your life—not consumes it
• The mindset shift from working harder to working smarter

Follow Alice on LinkedIn: https://www.linkedin.com/in/aliceheiman/

In this episode of Her Path to Revenue, Janelle breaks down a real client story that started with a familiar question:

- Should we move upmarket?
- Do we need ABM?

As companies begin to mature beyond SMB and leadership pushes for more predictable revenue, these questions come up more often—but the answer isn’t as simple as flipping a switch.

Janelle walks through how one company, already performing well on paper, realized their go-to-market motion wasn’t built to support an enterprise expansion. Instead of jumping straight into ABM, they took a step back to reassess what actually needed to change.

In this episode, you’ll learn:

• How to evaluate whether moving upmarket is the right next step
• Why account selection should be driven by data—not assumptions
• The shift from selling to individuals to engaging full buying groups
• What true alignment between marketing and sales actually looks like
• How this approach generated over $1M in qualified enterprise pipeline in 45 days

If you’re thinking about moving upmarket or exploring ABM, this episode gives you a practical, no-fluff look at what it really takes to make that transition work.

Melissa Moody doesn’t believe in chasing logos. She believes in doing work that actually matters—and building businesses that last.

In this episode of Her Path to Revenue, Janelle sits down with Melissa Moody—former Google leader, startup CEO, and now co-founder of Wednesday Women—to unpack what happens when you blend traditional SaaS growth with mission-driven business.

After 14 years at Google during some of the most transformative moments in marketing—search, mobile, video, programmatic—Melissa made the leap into early-stage startups and eventually into building a company of her own.

But Wednesday Women didn’t start as a business. It started as a simple idea: highlight one extraordinary woman every week.

That small ripple turned into something much bigger.

In this conversation, Melissa shares what it really takes to turn a mission into a sustainable company—and why so many founders struggle when emotion enters the equation.

From pricing challenges to building a business model that actually works, to the growing shift toward fractional leadership and redefining success on your own terms—this episode is equal parts tactical and deeply human.

If you’ve ever wrestled with aligning purpose and revenue, this one will hit.

In this episode, we cover:

• Why “the logo” doesn’t matter—and what actually does
• The biggest mistake founders make when building mission-led businesses
• Why pricing gets harder (and more emotional) when purpose is involved
• How Wednesday Women grew from a side project into a full business
• The rise of fractional leadership and what it signals about the market
• Why curiosity—not confidence—is the ultimate power move in leadership
• How to trust intuition alongside data when making career decisions

Connect with Melissa on LinkedIn: https://www.linkedin.com/in/melissammoody/

[WEBINAR] The Rise of Non-W2 Leadership: Why More Executive Women Are Rethinking Traditional Roles: https://watch.getcontrast.io/video-access?slug=wednesday-women-the-rise-of-non-w2-leadership-why-more-executive-women-are-rethinking-traditional-roles&token=YYmtkfZTkW8VoXeqndzo3fzf

Joelle Kaufman has built her career around one simple truth: curve balls aren't the exception — they're the whole game.

In this episode of Her Path to Revenue, Janelle sits down with Joelle Kaufman — 30-year tech executive, bestselling author, cancer survivor, and founder of Go-To-Market Flow — to unpack what it actually takes to build and scale revenue organizations when life keeps throwing you off course.

Before advising leaders on strategic revenue growth, Joelle spent three decades in the trenches — from negotiating what she believes was the first seven-figure AI contract in history as a business school student, to walking into a CEO's office seven months pregnant and saying "I should be your CRO." That willingness to shoot her shot — even when the odds were stacked — is what shaped everything about how she leads today.

Together, Janelle and Joelle dive into the real mechanics behind revenue leadership, including why reframing failure is the foundation of real confidence, how time constraints actually make you a better leader, and what most women get dangerously wrong about career advancement.

They also get into the human side of building an extraordinary career — from navigating pregnancy in the C-suite to battling cancer without slowing down, and why balance is a myth you need to stop chasing.

If you're a revenue leader, founder, or operator who's ever wondered how to keep climbing when life keeps interrupting, this conversation will change how you think about curve balls.

In this episode, we cover:

• Joelle's non-linear path from consulting to negotiating the first seven-figure AI contract in history
• Why she walked into her CEO's office seven months pregnant and asked for the CRO role
• How reframing failure is the real foundation of confidence
• What her best salesperson taught her about focus, qualification, and winning
• Why time constraints are actually a career superpower
• The myth of work-life balance — and what triage really looks like
• Her advice by decade: collect experiences in your 20s, focus in your 30s, lead boldly in your 40s

Follow Joelle on LinkedIn: https://www.linkedin.com/in/joellekaufman/

Kristy McCarley built her career around one simple truth: the audience you own will always outperform the audience you rent.

In this episode of Her Path to Revenue, Janelle sits down with Kristy McCarley — founder and managing director of Pure Firefly and the number one MailChimp partner agency in the US and Canada — to unpack what it actually takes to turn email into a real revenue engine for small businesses and nonprofits.

Before scaling Pure Firefly into a full-service agency supporting hundreds of brands, Kristy spent years navigating entrepreneurship as a solo operator, a mom, and a self-described introvert who had to learn how to own every room she walked into. That experience shaped everything about how she approaches marketing today — because when you've run a business where every decision has consequences, strategy stops being theoretical very quickly.

Together, Janelle and Kristy dive into the real mechanics behind email marketing and lifecycle growth, including why most businesses are still underestimating email as a revenue channel, how social media gives you reach but email gives you ownership, and what separates brands that see real ROI from those just sending blasts into the void.

They also get into the human side of building something from scratch — from navigating imposter syndrome and perfectionism to finding the confidence to keep going when the results take longer than expected.

If you're a founder, marketer, or small business owner trying to build a sustainable growth engine without blowing your budget on ads, this conversation will challenge how you think about the channels you invest in.

In this episode, we cover:

• Kristy's path from programming class to building the #1 MailChimp partner agency in North America
• What her first business taught her about email that changed everything
• Why you're renting your social audience — and what to do about it
• The real reason most email strategies underperform
• How to build and grow a qualified list that actually converts
• The patience and strategy it takes to see email marketing pay off
• Balancing entrepreneurship, motherhood, and showing up with confidence

Follow Kristy on LinkedIn: https://www.linkedin.com/in/kristymccarley/

Kathleen Booth has built her career around one simple truth: brand and revenue are not opposites.

In this episode of Her Path to Revenue, Janelle sits down with Kathleen Booth—B2B SaaS marketing leader, former agency founder, and now Head of Marketing at Sequel.io—to unpack what it actually takes to build sustainable growth in today’s market.

Before leading marketing inside some of the most respected communities and SaaS companies in tech, Kathleen spent over a decade building and scaling her own agency alongside her husband. That experience fundamentally shaped how she thinks about marketing today—because when payroll depends on revenue, marketing stops being theoretical very quickly.

Together, Janelle and Kathleen dive into the real mechanics behind revenue growth, including why community-led growth compounds over time, how challenger brands win market share during industry consolidation, and why marketers need to rethink the way they approach owned experiences and first-party data.

They also explore the human side of leadership—from balancing work and family seasons to building confidence in executive roles and taking the leap when the next chapter feels uncertain.

If you’re a marketing leader, founder, or operator trying to turn brand into real pipeline, this conversation will challenge how you think about growth.

In this episode, we cover:

• Kathleen’s unconventional path from international development to SaaS marketing leadership
• What entrepreneurship teaches you about revenue that corporate never will
• Why community-led growth creates compounding pipeline
• How challenger brands win when competitors consolidate
• The power of owned experiences and first-party intent data
• Why brand is a core revenue strategy—not a nice-to-have
• The reality of balancing career growth, leadership, and family

Follow Kathleen on LinkedIn: https://www.linkedin.com/in/kathleenslatterybooth/