In this episode of Revenue Career Ladder, Jamie Pagan is joined by Alina Vandenberghe to explore a journey of resilience, conviction, and rapid progression—from calculating utility bills at age eight to leading one of the most innovative SaaS platforms in the revenue space.

Alina shares powerful stories of her early entrepreneurial drive, her rise through the ranks in corporate America, and the lessons she’s learned as a founder navigating bootstrapping, hypergrowth, and team culture at scale. A raw and thoughtful discussion for anyone looking to fast-track their career or lead with purpose.

Expect to learn:

• Why resilience and discomfort early in life can fuel future leadership
• How listening—rather than arguing—is key to influencing senior stakeholders
• The real story behind the Reuters app launch on stage with Steve Jobs
• Why Alina walked away from a high-paid healthtech role to build from scratch
• Key hiring insights from scaling Chili Piper globally
• How to build and maintain company culture in a high-performance environment
• Why numbers, ownership, and empathy are foundational to career growth

Timestamps

00:00 - Introduction and guest welcome

01:14 - Alina’s first job at age 8 and early entrepreneurial mindset

10:42 - First major role at Reuters and the Steve Jobs keynote story

17:00 - Transition to director and lessons in influence and collaboration

23:12 - VP at Pearson and navigating corporate politics

32:36 - Misalignment in healthtech and decision to start Chili Piper

38:48 - Founding Chili Piper and discovering the first product

45:08 - Bootstrapping, VC funding, and evolving founder insights

53:04 - Hiring philosophies and adapting in the age of AI

58:04 - Decision-making culture and onboarding at Chili Piper

01:02:10 - Top 3 career tips and closing reflections

Ready to take the next step in your career journey? Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.

Unlock the power of data for both Marketing and Sales. With Dealfront, you can not only target the right prospects and run smarter campaigns but also empower your sales team to close deals faster by aligning them with high-intent accounts. Drive sustainable revenue growth and maximize ROI across both sides of the funnel with one seamless solution.

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Alina Vandenberghe: 

LinkedIn: https://www.linkedin.com/in/alinav/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

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X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In the opening episode of Season 2 of Revenue Career Ladder, host Jamie Pagan is joined by Tom Boston for a candid and often hilarious deep dive into the unorthodox career path that took him from a DIY store cashier to a standout brand voice in B2B SaaS.

Tom shares how moments of feeling lost, accidental detours, and pivotal support from others shaped his eventual discovery of a unique professional lane—one that blends creativity, comedy, coaching, and content. This episode is a heartfelt conversation about figuring it out late, staying true to your voice, and building a career by embracing what makes you different.

Expect to learn:

• How retail and acting prepared Tom for a career in B2B sales
• Why “being yourself” is a strategic advantage in sales and branding
• The unlikely moment that kickstarted Tom’s content career
• What it’s really like building a personal brand from scratch on LinkedIn
• How content, coaching, and career alignment came together at MySalesCoach
• The importance of mentorship, honesty, and figuring out your strengths
• Why it's okay—and even helpful—to feel lost early in your career

Ready to take the next step in your career journey? Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.

Unlock the power of data for both Marketing and Sales. With Dealfront, you can not only target the right prospects and run smarter campaigns but also empower your sales team to close deals faster by aligning them with high-intent accounts. Drive sustainable revenue growth and maximize ROI across both sides of the funnel with one seamless solution.

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Tom Boston: 

LinkedIn: https://www.linkedin.com/in/tom-boston/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

After a breakout first season, Revenue Career Ladder is back — and we’re going even deeper.

Season 2 brings fresh voices and candid career conversations from standout professionals across SaaS. From SDRs-turned-founders to marketing leaders breaking new ground, each guest opens up about the pivotal moments, mindset shifts, and messy middle chapters that shaped their journey.

Whether you’re aiming for your first promotion or eyeing the C-suite, this season delivers real-world advice for climbing with confidence — no corporate clichés required.

Expect honest conversations. No fluff. Just practical insights from people who’ve been in the trenches and made bold moves in sales, marketing, RevOps, and beyond.

Hit play on the trailer to hear what’s coming.

Season 2 launches August 25th.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Jamie Pagan:

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us:

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan sits down with Hannah Ajikawo, CEO and Founder, to discuss her journey from working at a local food market stall to running her own successful business. 

Throughout the conversation, Hannah shares the lessons she learned from her early career experiences, the challenges she faced in the corporate world, and the unique approach she takes in consulting today.

Hannah dives into how she navigated leadership transitions, dealt with cultural challenges, and ultimately found her way into the world of entrepreneurship. She also talks about her passion for helping others achieve success, particularly those who come from underrepresented backgrounds.

Expect to learn:

• The value of early work experiences, even if unpaid, in shaping your career
• How to assess whether a company's culture aligns with your values during the interview process
• The importance of resilience when dealing with challenges like bullying or poor company strategy
• Insights into navigating leadership roles and driving change within organizations
• How to approach consulting and offering value to businesses by understanding go-to-market strategies

Ready to take the next step in your career journey? 

Subscribe to Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Hannah Ajikawo: 

LinkedIn: https://www.linkedin.com/in/hannah-ajikawo/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan is joined by Ben Smith, whose career journey has taken him from Professional Ice Skater at Disney on Ice to Marketing Director.

Ben shares his unique path into marketing, reflecting on his early work experience, including his time with Youth Parliament, as well as the entrepreneurial mindset he developed through his family’s businesses.

Ben discusses the valuable lessons he’s learned along the way, particularly around taking risks, stepping out of his comfort zone, and always striving for growth.

He also highlights how early roles in hospitality and PR shaped his approach to marketing and gave him a fresh perspective on business development.

Expect to learn:

• How early roles, like pot washing, can spark an entrepreneurial mindset and shape your future career
• The importance of understanding both marketing and sales, and how they work together to drive business success
• Why taking on extra responsibilities—without always being paid for them—can fast-track your career growth
• How to navigate career transitions, especially when moving between different functions and industries
• Key insights into the hospitality industry and how those experiences shaped Ben’s later career in B2B marketing

Ready to take the next step in your career journey? 

Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Ben Smith: 

LinkedIn: https://www.linkedin.com/in/bensmith-reachdesk/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan sits down with Mafalda Johannsen, who shares her journey from working as a travel sales agent to becoming the Head of Business Development. Mafalda discusses her career trajectory, which spans multiple industries—from tourism to tech—and the skills she gained along the way. 

She offers an honest reflection on how overcoming challenges, including a 100% commission job, shaped her approach to sales and leadership. Mafalda also talks about her transition into the tech industry and the impact of her diverse experience in driving growth and success in her current role.

Expect to learn:

• The value of starting in a challenging, commission-based sales role and how it prepares you for future career success
• Why moving to the tech industry was a strategic decision for Mafalda and how it shaped her career
• Key skills Mafalda gained in the tourism industry that are applicable to business development and sales in tech
• Insights into how the startup environment accelerates career growth and learning
• The importance of building a thick skin and managing customer expectations
• How Mafalda leveraged her past experience to create effective sales enablement and onboarding processes in new roles
• Career advice on handling transitions and evaluating your potential for growth in different companies

Ready to take the next step in your career journey? 

Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Mafalda Johannsen: 

LinkedIn: https://www.linkedin.com/in/mafalda-johannsen-007489a4/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan speaks with David Wilkins, an experienced sales leader and entrepreneur, about his journey from bookseller to founder. 

David shares his unconventional career path, including his time as a rugby coach, working in various sales roles, and eventually stepping into the entrepreneurial world. He offers valuable insights into what it takes to succeed in sales and how he navigated his career to build a successful business in the tech world.

David talks about the lessons learned during his time at Palo Alto Networks and Infoblox, his transition from sales to leadership, and his experience as a director of sales development. He also discusses the challenges of navigating a career while staying true to personal values and goals, particularly in the competitive world of SaaS.

Expect to learn:

• How working as a bookseller shaped David’s understanding of human behavior
• The role that passion and coaching played in David’s decision to follow a non-traditional career path
• Insights on how early jobs taught David the importance of navigating workplace dynamics and human behavior
• Key takeaways from David's transition into tech sales, including overcoming challenges in the business development role
• The value of mentorship, trust, and leadership in growing a career
• How to manage career growth and handle challenges like layoffs and career changes with resilience
• The importance of having a clear career plan, setting personal goals, and being transparent with managers about career aspirations

Ready to take the next step in your career journey? 

Subscribe to Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow David Wilkins: 

LinkedIn: https://www.linkedin.com/in/daveewilkins/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan is joined by Neil Bhuiyan, the founder of HappySelling. Neil’s career trajectory is an insightful story of perseverance and reinvention, transitioning from a young person with a difficult relationship with authority to a leader in sales training and coaching.

Neil opens up about his early work experiences, from his first job in a fish and chip shop to his role in local government, which shaped his approach to problem-solving and customer service. He then shares how his introduction to technology and the SaaS industry marked the start of his journey into tech sales. 

Neil details his career progression through multiple roles at companies like Zuora and Showpad, eventually finding his true calling in customer success, where he found fulfillment helping sales teams thrive.

Expect to learn:

• How early work experiences in customer-facing roles built Neil’s resilience and understanding of client needs
• The importance of self-awareness and personal growth in overcoming challenges and finding career direction
• The difference between transactional sales and the value of building lasting client relationships
• Key lessons from Neil's time as an SDR, including how he built pipeline from scratch and navigated the challenges of the startup environment
• Insights into transitioning from sales to customer success and the value of understanding both sides of the business
• The role of leadership and mentorship in helping others develop and succeed in sales
• How Neil used his background in sales to enhance customer success, including strategies for upselling, retention, and working with both sales and marketing teams

Ready to take the next step in your career journey? 

Subscribe to Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Neil Bhuiyan: 

LinkedIn: https://www.linkedin.com/in/neilbhuiyan/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of The Revenue Career Ladder, host Jamie Pagan speaks with Tom Hunt, the founder of Fame, a B2B podcast agency that helps businesses leverage podcasts for growth. Tom takes us through his unconventional career journey—from working in a family-run takeaway to launching multiple entrepreneurial ventures, before settling on creating one of the most successful podcast agencies in the industry.

Tom reflects on his time at Ernst & Young and Accenture, where he honed his people management and consulting skills, before deciding that being employed wasn’t for him. His entrepreneurial journey began with a small leggings business, then evolved into running podcasts and building Fame, which focuses on creating and promoting podcasts for B2B companies. 

Tom shares how he managed to combine his experience in consulting with his passion for marketing and how this led to the creation of Fame, which now helps clients grow their audiences and generate leads through strategic podcasting.

Expect to learn:

• How Tom’s early work in a family takeaway taught him valuable lessons about responsibility and attention to detail
• The benefits of working in large consulting firms like Ernst & Young and Accenture and how they shaped his approach to managing people and running meetings
• The power of leveraging personal brand and audience-building strategies for B2B marketing
• How creating podcasts for sales and marketing teams can significantly boost visibility and generate new business
• Key lessons from Tom’s entrepreneurial ventures, including the importance of sticking with a successful business idea rather than jumping to the next project
• How to use freelancing as a stepping stone to create a scalable business
• The value of focusing on freedom and personal growth in your career, and why it’s essential to do what aligns with your core values

Ready to take the next step in your career journey? 

Subscribe to Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Tom Hunt: 

LinkedIn: https://www.linkedin.com/in/tomhuntio/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront

In this episode of Revenue Career Ladder, host Jamie Pagan sits down with Daan Matthes, a seasoned sales professional turned entrepreneur. Daan shares his journey from his humble beginnings in call centres to becoming a sales leader at top startups and eventually founding his own company. 

This candid conversation covers pivotal career decisions, lessons learned from failures, and insights on navigating the fast-paced world of sales leadership. Whether you're climbing the revenue career ladder or charting your own entrepreneurial path, Daan's story is filled with actionable advice and inspiration.

Expect to learn:

• Why building relationships in a new job is everything.
• How to turn career missteps into stepping stones.
• The secret to hiring the right first team members.
• Why startups are like rocket fuel for your career (and how to handle the chaos).
• Daan’s honest take on moving from being a top performer to leading a team.
• A sneak peek at how he’s using AI to shake up sales enablement.

Ready to take the next step in your career journey? 

Subscribe to Revenue Career Ladder today and start making your professional aspirations a reality.

—

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Daan Matthes: 

LinkedIn: https://www.linkedin.com/in/daanmatthes/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: 

LinkedIn: https://www.linkedin.com/company/dealfront/

Facebook: https://www.facebook.com/getdealfront/

Instagram: https://www.instagram.com/getdealfront/

TikTok: https://www.tiktok.com/@dealfront

X: https://x.com/getdealfront

YouTube: https://www.youtube.com/@dealfront