Higgle: The B2B Sales Club

What happens when your biggest sales advantage suddenly disappears overnight? In this episode I sit down with Kris Rudeegraap, Co-CEO and Co-Founder of Sendoso. In this first of two parts, we rewind to the scrappy early days of his business when Kris was manually packing boxes at night just to stand out in sales. Kris shares how a personal frustration inside his own sales role sparked the idea for the platform that would later raise over $150 million in funding. We talk about pre-selling before the product is ready, building momentum through outbound, and why he refuses to wait for perfection before talking to customers. Kris breaks down the critical decisions that transformed early traction into scalable growth. He explains why hiring external salespeople early is essential to proving true product-market fit, how strategic tech partnerships accelerate momentum, and what it actually feels like to jump from $1M to nearly $5M in a year. We explore the realities of raising multiple funding rounds, building repeatable systems, and surrounding yourself with advisors who have seen the movie before. This all sets up part 2, where we'll take a close look at the advantages of using physical gifting to grow B2B relationships. Topics covered during this episode include: Listen in to uncover the early decisions that shaped a nine-figure growth journey. Kris Rudeegraap on LinkedIn: https://www.linkedin.com/in/rudeegraap

In this episode we're welcoming Chris Davis, Managing Director (UK) at Hypetap, to unpack what influencer marketing really means beyond the buzzword. He explains why trust beats follower count, and how the algorithms have quietly rewritten the rules. Chris explains how a creator with a thousand followers can now outperform someone with a million, and why authenticity is the real currency that brands care about. Then, we turn the lens specifically towards B2B. I challenge Chris on what influence looks like in professional services, on LinkedIn, and inside niche industries. We talk about why going viral doesn't necessarily generate business, what changed in his own content strategy, and how misunderstanding what a client needs can kill a deal. We explore the tension between thought leadership and commercial intent, the rise of AI-written noise, and why consistency still wins every time. Topics covered during this episode include: Listen now to uncover what's changing in influencer marketing before your competitors do! Chris Davis on LinkedIn: https://uk.linkedin.com/in/chris-davis-01107318

Are traditional go-to-market models quietly collapsing under the weight of AI? I'm picking up the conversation with Nikki Barua today by looking at what reinvention actually means when agentic AI reshapes sales, marketing, and go-to-market teams in real time. We talk about why old formulas built on volume, velocity, and hustle are breaking down, and why mass personalization is eroding trust instead of building it. Nikki explains how leaders must shift from chasing output to building outcomes, rethinking everything from funnels to pricing models. The conversation quickly expands beyond tools into decision-making chaos, longer buying cycles, and the growing pressure facing executives across industries. Nikki examines what happens when entire sectors feel the shockwaves of AI overnight and why slow, cautious moves may be more dangerous than imperfect action. She walks through how organizations can approach reinvention systematically and why static transformation plans no longer survive reality. We dig into what truly changes when companies commit to ongoing reinvention, how leadership teams align around uncertainty, and why people, not technology, ultimately determine whether AI becomes a moat or a meltdown. Topics covered during this episode include: Tune in and discover what it takes to adapt when transformation never ends! Nikki Barua on LinkedIn: https://www.linkedin.com/in/nikkibarua

What does it really take to shed an old identity and build an entirely new one from scratch? I sit down with Nikki Barua, Co-Founder of FlipWork, this week for the first of a two-parter. We go straight into the idea of reinvention, not as a buzzword, but as a lived experience shaped by survival, identity shifts, and relentless curiosity. We talk about how Nikki arrived in a new country with no resources, no safety net, and the uncomfortable reality of having to unlearn deeply held beliefs just to move forward. Nikki shares how reinvention isn't just about changing habits or careers, but about letting go of parts of yourself, confronting grief, and rebuilding identity from the inside out. We explore how belief systems evolve over time and why identity (not behaviour) is the real engine of change. We move through stories of role models, courage in unfamiliar systems, and the slow, often invisible work of rewiring how you think, speak, and show up. Nikki also begins to connect these personal reinvention themes to much larger questions about organizations, leadership, and the future of work. It sets the stage for what's coming in part two, hinting at how individual transformation scales into workforce reinvention in an era defined by constant disruption. Topics covered during this episode include: Start listening now and set the foundation for a much bigger conversation about the future of work! Nikki Barua on LinkedIn: https://www.linkedin.com/in/nikkibarua

Are you missing out on consistent revenue because you don't truly understand how partnerships actually work? Dave Plunkett, Founder of Collaboration Junkie, joins us today to unpack what partnerships really are and why so many agencies don't utilize them properly. He explains the critical difference between referrals and true commercial partnerships, and why trust-based selling is becoming more powerful as outbound becomes noisier and less credible. Dave introduces his D.A.N.C.E. framework and challenges common assumptions about cross-referrals, tech partnerships, and why "having lots of coffees" doesn't equal a strategy. As we continue, we explore how to design systems that make partnerships scalable, how to reward referrals without creating awkward incentives, and why most businesses obsess over finding partners before doing the foundational work. Dave shares real examples of agencies generating significant revenue in just weeks by activating relationships they already have. We talk about ecosystem mapping, value chains, commercialization, co-marketing with tech platforms, and the subtle but powerful art of nurturing long-term trust. Topics covered during this episode include: If you want partnerships that actually generate revenue, listen now and learn this incredible framework! Dave Plunkett on LinkedIn: https://www.linkedin.com/in/daveplunkett/

Are we hiding behind sales tech instead of actually knowing how to sell? Joe Fontana, Advisor / Founding VP of Sales at Dextego, is a sales leader who's been building teams since the 90s. In this episode, we go straight into the tension that's shaping modern B2B selling. We talk about why sales and marketing still struggle to align, what's broken about incentives and KPIs, and why SDR teams might belong inside marketing. Joe challenges the way we think about prospecting today, especially the growing dependence on automation and AI. As we unpack what's changed (and what hasn't), we realize we're circling a bigger question about whether sellers truly understand the fundamentals anymore. From cold calling myths to LinkedIn prospecting strategies, we look at what actually works in 2026. Joe shares hard truths about technology becoming a crutch, why most sellers couldn't survive without their tools, and what it really means to "come correct" when approaching a buyer. We explore why big deals can't be closed over email, how fear still drives avoidance of the phone, and what buyers actually need from sellers today. Topics covered during this episode include: Hit play now and rethink everything you've assumed about modern B2B selling! Joe Fontana on LinkedIn: https://www.linkedin.com/in/joe-fontana75/

Has modern B2B sales become so automated that going "backwards" is actually the smartest move? Today we've got Stephanie Melodia, keynote speaker and Creator of Hacking Luck, and Tash Rebuck, Founder of TR Sales Consultancy, joining us to unpack what's really happening in B2B sales right now (and some of it is wildly unexpected). Tash shares why traditional outreach methods like cold calling and physical gifting are making a serious comeback, complete with superb response rates that leave mass AI email campaigns in the dust. Tash provides examples of outrageous but brilliant campaign ideas, the surprising data behind them, and why sending something tangible can spark conversations that digital channels simply can't. From there, I discuss the tension between sales and marketing with Stephanie, exploring why alignment can still feel elusive. We talk about the challenge of attribution in long B2B sales cycles, the fear around investing without immediate ROI, and the power of a single "north star" metric to unite teams. There's also a fun conversation about persuasion at the leadership level, experimentation, and what it really takes to drive net new growth in a noisy, skeptical market. Topics covered during this episode include: Don't let outdated tactics hold you back. Listen now and explore bold new ways to win enterprise deals! Stephanie Melodia on LinkedIn: https://www.linkedin.com/in/stephmelodia-keynotespeaker/ Tash Rebuck on LinkedIn: https://www.linkedin.com/in/tashrebuck/

How do you build real momentum when relationships, timing, and trust refuse to move in straight lines? I'm sitting down with Alice Dawlat, Director of Growth & Partnerships at REF Digital, letting you in on what business development really looks like when you come from a delivery-first background. We talk through her path from project management into leading growth, and why that transition is far more emotional and uncertain than most people expect. She shares how structure, organization, and precision don't disappear, they just have to evolve. We get into the uncomfortable moments where certainty doesn't exist yet, how trust is built before a contract is signed, and why the hand-off between selling and delivery can make or break everything. Later, we walk through what it takes to move from inbound opportunities to a deliberate outbound strategy. Alice talks about picking a niche, deciding who not to chase, and building credibility with people who don't know you yet. The conversation then explores how relationships start long before projects, why timing matters more than pressure, and how growth depends on resilience, alignment, and staying human in every interaction. Topics covered during this episode include: Check out this episode and discover why patience and clarity beat pressure every time! Alice Dawlat on LinkedIn: https://www.linkedin.com/in/alicedawlat/

Can you believe that small moments of trust and safety matter more than any sales technique? In this second of two parts with Mike Mears, we shift the focus directly into sales, leadership, and the psychology behind real influence. We explore what Mike has learned throughout his career, including why one-way communication fails and how dialogue reveals what leaders often miss. The discussion quickly moves into how assumptions quietly damage sales performance, why curiosity consistently outperforms pressure, and how traits can shape success in sales. As the episode continues, we get into the path of safety, trust, clarity, and challenge, plus why skipping any step undermines everything that follows. We unpack social pain, how easily it's triggered, and why the brain remembers it longer than physical injury. Mike explains why trust is fragile, how consistency outweighs charisma, and how even small facial expressions can create lasting damage. Mike leaves us by talking about how steady course correction beats dramatic intervention when it comes to motivating teams and driving growth. Topics covered during this episode include: Uncover the unseen forces influencing trust, motivation, and performance in this episode! Mike Mears on LinkedIn: https://www.linkedin.com/in/mike-mears-leadership-theoretician-4627a889/ The Check-in Cheat Code: https://piscari.com/wp-content/uploads/2026/01/Checkin-Cheat-Sheet.pdf The 15 Powerful Intrinsic Rewards: https://piscari.com/wp-content/uploads/2026/01/Intrinsic-Rewards.pdf

How do trust, certainty, and human behaviour decide outcomes when the stakes are extreme? In this first part of a two-part conversation, I'm welcoming Mike Mears, a former Chief of Human Capital at the CIA, to explore the hidden mechanics of leadership and human behaviour under immense pressure. We start with his unlikely path from West Point and Harvard Business School into covert intelligence work, and how that experience exposes patterns most people never get to see. From working undercover in dangerous environments to later building the CIA Leadership Academy, Mike shares stories that reveal how trust, fear, and certainty quietly drive human decisions before logic enters the picture. We examine how leaders influence behaviour when authority alone doesn't work, and why clarity matters more than motivation. Mike explains how the CIA studies cognitive bias, uncertainty, and insight moments in the brain, along with why those discoveries matter far beyond espionage. We also look into how certainty is created, why people hesitate even when solutions look obvious, and how small behaviours can shift outcomes in high-stakes situations. Topics covered during this episode include: Listen now to explore how certainty and trust influence outcomes long before logic does! Mike Mears on LinkedIn: https://www.linkedin.com/in/mike-mears-leadership-theoretician-4627a889/ The Check-in Cheat Code: https://piscari.com/wp-content/uploads/2026/01/Checkin-Cheat-Sheet.pdf The 15 Powerful Intrinsic Rewards: https://piscari.com/wp-content/uploads/2026/01/Intrinsic-Rewards.pdf

Why is mass personalization with AI actually making it harder to win deals? I sit down with Freya Ward, Associate Managing Director at Headley Media, for her second appearance on the show to unpack how the B2B buying journey has fundamentally changed...and why so many sales strategies are now misaligned with reality. We dig into the shift toward long, independent research cycles and the rise of "hidden buyers" who shape decisions without ever speaking to sales. We explore why awareness, familiarity, and internal justification matter more than pushing for sales-ready leads, especially when buying committees are larger, risk-averse, and under pressure to justify decisions internally. We also get into the impact of AI, personalization, and data on trust. We examine why mass personalization often backfires, how buyer fatigue is quietly eroding confidence, and why more content doesn't always mean more influence. Freya breaks down the differences between first-party and zero-party data, how explicit intent changes engagement, and why true personalization still requires human effort. Topics covered during this episode include: Listen now to uncover what's quietly shaping buying decisions long before sales ever gets involved! Freya Ward on LinkedIn: https://www.linkedin.com/in/freya-ward/

Can a fairly short book really build authority faster than years of content marketing? Julie Trelstad, Head of US Publishing at Amlet.ai, joins me this week to unpack how books quietly remain one of the most powerful tools for building authority and trust. Julie shares insights from her decades of publishing experience to explain why a book doesn't need to be long or traditional to be impactful. We talk about narrow points of view, short-format books, and why speed to market often matters more than prestige. She shares how credibility is baked into authorship itself, and how professionals can carve out a "category of one" by publishing focused, practical ideas instead of overwhelmingly long reads. We then explore the real mechanics behind publishing today, including self-publishing, hybrid models, and why discovery almost never happens on Amazon. Julie also gives advice on how AI can support the writing process without replacing the author's voice, and why emerging ideas around digital rights and content licensing may redefine how expertise is monetized. Topics covered during this episode include: Check out the incredible insights in this chat to discover how a short, focused book can instantly elevate credibility and open new opportunities! Julie Trelstad on LinkedIn: https://www.linkedin.com/in/julietrelstad

What actually cuts through when buyers ignore almost every email and call? I'm welcoming Mike Fantis, VP Managing Partner at DAC Group/London, to unpack what's really happening in modern sales and why so much outreach simply doesn't work anymore. We talk about how digital convenience has created lazy habits, from bulk emails to hollow personalization, and why buyers have learned to tune it all out. He explains that tactics are not as important as the fundamentals: value, relevance, and understanding how businesses actually operate. Mike explains why long-term relationship building, pipeline thinking, and showing insight before there's ever a brief are extremely important. We get into how pitches are really won before anyone enters the room, why chemistry and clarity matter more than volume, and how agencies lose by trying to be everything to everyone. Mike also shares insights on omnichannel disconnects, retail blind spots, and why answering today's brief isn't enough without planning for tomorrow's business reality. Topics covered during this episode include: Don't miss this conversation on standing out when everyone sounds alike! Mike Fantis on LinkedIn: https://www.linkedin.com/in/michaelfantis/

Can saying no to a perfect deal actually unlock a bigger win? I'm joined by Phil Squire, and we explore what really drives success in complex sales when trust, access, and credibility are on the line. We talk through research that shows dramatic shifts in win rates when teams focus on a small set of positive mindsets—and what changes when organizations stop chasing every opportunity. We dig into the real cost of bidding, why some tenders are unwinnable before they start, and how procurement processes can unintentionally block the very behaviors buyers say they value. Along the way, Phil shares a story that turns conventional sales logic upside down. We then move beyond stories into what's changed since the original research. I walk through how mindset can be measured, practiced, and developed over time, and why most sellers still fall short even when they think they're doing well. We explore why values are different from personality, how leaders shape behavior through systems and incentives, and why the rise of AI is raising expectations instead of lowering them. The conversation closes with a sharp look at originality, authenticity, and what it now takes to be genuinely credible in front of skeptical buyers. Topics covered during this episode include: Prepare to be fascinated when you hear why doing less can sometimes win you far more! Phil Squire on LinkedIn: https://www.linkedin.com/in/philipsquire/

Why do most sales conversations quietly fail before anyone realizes what went wrong? Today, I sit down with Philip Squire, CEO of Consalia, to explore a research journey that begins with a deceptively simple question: how do customers actually want to be sold to? In this first of a two-part series, we go back to the early interviews that sparked his doctoral research, where senior buyers openly shared stories of sales conversations that worked (and far more that didn't). We reflect on the surprising intensity of their responses, the emotional energy behind their frustrations, and how a single off-script question revealed just how few salespeople are getting it right. We follow the evolution from early data collection into a much deeper inquiry about what really drives sales behaviour, checking out why traditional competency models fail to explain buyer dissatisfaction, as well as how a pivotal shift can reframe everything around values rather than tactics. Philip finishes up part one by giving a preview of some of his findings that challenge long-standing assumptions about selling. Topics covered during this episode include: . Check out this episode to hear the research that reframes what buyers really respond to! Philip Squire on LinkedIn: https://www.linkedin.com/in/philipsquire/

What happens when brilliant delivery is no longer enough to keep clients loyal? It's time to explore what truly drives sustainable agency growth by unpacking two decades of relationship data with Emma Hillary, Head of Growth & Marketing at Verity Relationship Intelligence. We focus on why great work alone no longer guarantees retention, even when client satisfaction appears high. Emma breaks down the findings of Verity's 2025 Relationship Report, which identifies six traits shared by high-performing agencies, challenging the assumption that results always come first. We dig into why understanding clients as humans, not just as briefs or businesses, creates a stronger foundation for trust, confidence, and long-term value. Emma explains what's happening beneath the surface of modern client–agency relationships, and we talk about efficiency complaints, post-pandemic pressure, and why relationships often become strained even when delivery improves. We examine the hidden cost of transactional behaviours, the imbalance that can form between clients and agencies, and how feedback can become a growth lever instead of a threat. Finally, we look into why team satisfaction is declining while client ratings rise, and what that tension reveals about the future of agency models. Topics covered during this episode include: Uncover what really keeps clients committed beyond the work itself in this episode! Emma Hillary on LinkedIn: https://www.linkedin.com/in/emma-hillary-49b5aa9/

What if the biggest sales opportunities you're missing could be unlocked simply by changing how you follow up? We're talking with Evelyn Oluwole today, AKA "The Follow-Up Queen," digging into the experiences that shaped her journey to leading major global accounts. Evelyn, who is the Senior Sales Director at WeTransfer, challenges the assumptions many of us carry about what real selling actually requires. She opens up about why legitimately listening to potential clients still beats every piece of technology, how knowing just two pieces of information can transform a cold call, and why she believes sales remains the least-trained yet most business-critical profession. Evelyn then talks about her impressive expertise in follow-up conversations, along with why she thinks most deals fall apart not because of a bad pitch, but because the strategy afterward is weak or non-existent. She shares how timing, value, and multi-touch outreach can completely change the trajectory of a deal, and she breaks down a recent six-figure win that came from persistence, intention, and the right kind of visibility. We also discuss how AI can elevate, not replace, the work we do, and why using it well could become the next major competitive edge. Topics covered during this episode include: Listen now to discover the strategies that turn conversations into real opportunities! Evelyn Oluwole on LinkedIn: https://www.linkedin.com/in/evelynoluwole/ Evelyn Oluwole on Instagram: https://www.instagram.com/thefollowupqueen/

What if the key to closing more sales lies in understanding body language and reading the room effectively? Kevin Kelly, an international keynote speaker and author, takes us through his Three A's framework (awareness, attention, and action) in this episode. We explore the secrets to forming genuine connections with clients, where likability and trustworthiness take center stage. Curious about how self-awareness can boost your sales game? Kevin and I unpack this fascinating topic, offering compelling stories that highlight how understanding yourself can reshape your interactions and lead to greater sales success. As we navigate the evolving B2B sales landscape, we offer powerful insights on engaging buyers early and building lasting client relationships. Ever wondered how storytelling can revolutionize your sales conversations? Kevin shares captivating experiences, illustrating how aligning your narrative with clients' needs can transform them into loyal advocates. We also tackle the art of reading body language and why resilience and patience are key tools for any salesperson. Topics covered during this episode include: Transform your approach to sales by mastering the Three A's framework and enhancing communication! Kevin Kelly on LinkedIn: https://www.linkedin.com/in/kevinkelly1/

Could the power of active listening and effective questioning be the missing link to winning more sales? We're getting deep into the art of crafting persuasive sales presentations with the insightful Tom Martin, Founder & President of Converse Digital, in this episode. Together, we unlock the secrets of using authenticity and vulnerability to transform ordinary pitches into extraordinary ones. Are you tired of feeling like your presentations fall flat? Discover how embracing imperfections and structuring your arguments clearly can resonate more with your audience. Plus, Tom reveals the science behind managing your audience's cognitive load, ensuring your message sticks long after the presentation ends. We also explore the critical role of active listening in sales calls. Ever wondered why some pitches just don't land? We tackle the pitfalls of confrontational language and the magic of asking insightful questions. Tom and I uncover how truly engaging with clients can lead to unexpected insights and lasting partnerships, with tips that will allow you to revolutionize your sales approach and win over clients with genuine connections. Topics covered during this episode include: Tune in to discover the secrets of crafting persuasive sales presentations and learn how authenticity and active listening can transform your pitch! Tom Martin on LinkedIn: https://www.linkedin.com/in/tommartinjr/

What are the often-overlooked red flags and chemistry factors that can make or break your agency's success in the RFP process? I'm thrilled to welcome Michelle Cleary, a seasoned marketing procurement professional with Anywhere Real Estate, to unravel the myths and unlock the potential of procurement in agency collaborations. Michelle shares her unique insights into how early engagement with procurement can transform it from a perceived bureaucratic hurdle into a strategic partner that adds immense value. We discuss the art of procurement, exploring how it can foster strong, successful relationships and elevate agency performance. As we continue on, Michelle sheds light on the complexities of the agency selection process and the nuances of running a successful RFP. She emphasizes the importance of embracing niche expertise and recognizing the value of team chemistry in building successful partnerships. Michelle offers practical advice on how agencies can stand out, adapt to client needs, and build trust through transparency and personal interactions. Topics covered during this episode include: Don't miss this episode to gain actionable insights on navigating agency selection and RFP processes for standout marketing strategies! Michelle Cleary on LinkedIn: https://www.linkedin.com/in/michelle-c-b3828b9/