The struggle of saying “yes” with Will Aitken

On this week's episode of the award winning Bold Calling podcast, host Adam Sockel sits down with Kevin Hopp, founder of Hopp Consulting Group and CEO of Calling Culture, to discuss why cold calling remains a powerful tool in a world obsessed with automation and AI. Kevin shares his candid insights on the current state of sales development, debunking the myth that cold calling is a thing of the past. They delve into the nuances of outbound strategies, the role of AI in sales, and why businesses need to embrace a calling-first mindset for real human connection. Key Takeaways Cold Calling Renaissance: Despite AI and automation trends, Kevin argues that cold calling remains irreplaceable for genuine, high-value conversations. Smaller Budgets, Smarter Strategies: As outbound budgets shrink, teams are optimizing their approach by focusing on impactful cold calling over bulk outreach methods. Efficient Pre-call Research: Kevin believes most reps over-prepare, wasting hours on unnecessary details. The key? Know the core business problem and solution. Data-Driven Insights: Capturing and leveraging call outcomes—beyond just booked meetings—is essential for informing CRM strategies and account-based marketing. Future of Sales Development: While AI tools may evolve, they’re not replacing the human element anytime soon. Sales is still about people selling to people. Memorable Quotes “Cold calling ain’t dead. The more confusing outbound gets, the more valuable a straightforward phone call becomes.” — Kevin Hopp “Reps need way less research than they think. Focus on the business problem and solution—it’s all that matters.” “The tools are getting smarter, but the human connection of a live conversation on the phone can’t be replaced.” Why Listen? If you're navigating the ever-changing landscape of sales development or wondering how AI will shape outbound, this episode is packed with actionable advice. Kevin Hopp’s expertise is a must-hear for SDRs, managers, and sales leaders who want to embrace smarter, human-centered strategies. Resources Mentioned Hopp Consulting Group Kevin’s TikTok-style sales tips on LinkedIn Connect with Us Host: Adam Sockel on LinkedIn Guest: Kevin Hopp on LinkedIn Presented by Orum, the #1 dialer for sales teams in 2025! Love the episode? Share it with your team and leave us a review! Want to dive deeper into sales development insights? Subscribe to Bold Calling for more conversations that matter.

In this episode of Bold Calling, Adam sits down with Michael Maximoff, founder of Belkins, to explore the evolving world of sales development and how SDR roles are shifting amidst advancements in AI, automation, and omnichannel strategies. They dive into Orum's 2024 State of Sales Development Report findings, touching on the increased demand for SDRs, shifts in sales pipeline responsibilities, and the critical alignment of sales and marketing functions. Key Topics Discussed: The Changing SDR Role Michael shares insights on how SDRs are becoming growth specialists who strategically build omnichannel outreach strategies rather than relying solely on single channels. SDR roles are evolving into "GTM growth specialists," responsible for managing multiple channels to nurture leads more effectively. Omnichannel Outreach vs. Multichannel Marketing Michael distinguishes between true omnichannel strategies and basic multichannel outreach, emphasizing the importance of seamless, personalized customer journeys that guide prospects from awareness to conversion. The Power of the Phone in SDR Outreach According to Orum's report, 85% of sales leaders view phone calls as essential for building pipeline, with 70% saying over half of their pipeline results from calls. Michael adds that phone outreach works best when it’s the third or fourth touchpoint after establishing prior contact through other channels. Balancing AI and Human-Centric Sales Strategies Despite the rise of AI, Michael argues that human-led sales strategies are more impactful, particularly for creating long-term customer relationships. He predicts a growing divide between companies that use AI for efficiency and those prioritizing genuine customer connections. Optimizing SDR Teams and Specialization Michael explains Belkins’ team structure, which includes lead researchers and SDRs working in tandem to ensure high-quality outreach. By specializing roles, Belkins maximizes efficiency and effectiveness, allowing SDRs to focus on engaging leads without being bogged down by list-building. The Future of Sales Development Michael forecasts that SDRs will increasingly contribute to strategy development alongside traditional outreach. The demand for nuanced, high-impact touchpoints will only increase as companies navigate growing volumes of outreach driven by automation. Key Quotes: On Omnichannel Outreach: “Omnichannel isn’t just using multiple channels; it’s an integrated, step-by-step approach where each touch builds on the previous engagement, creating a seamless customer experience.” On the Role of the Phone: "The phone is incredibly effective, but it shouldn’t be the first touchpoint. Using it as a third or fifth touchpoint after nurturing leads through other channels makes conversion rates three to five times higher." On the Importance of Human Sales: “With AI, we’re seeing a rise in volume over quality. Brands that build real relationships with prospects and foster strong teams will ultimately stand out in a market flooded with automated outreach.” Connect with Michael Maximoff: LinkedIn: Michael Maximoff Podcast: Belkins Podcast on YouTube Email: [email protected] Tune in to this episode for a comprehensive discussion on the modern SDR landscape and how sales teams can leverage both technology and human touch to create impactful outreach in today’s market.

In this episode of Bold Calling, Adam Sockel sits down with Troy Barter, Head of Revenue at Rocket Shipping, to dive into the nitty-gritty of sales development. Troy brings his extensive sales experience, from door-to-door hustle to tech sales strategy, to offer hard-hitting insights on the evolution of the SDR role, the power of resilience, and the real impact of sales development. Key Highlights: The Value of Perspective in Sales Development: Troy draws a powerful comparison between door-to-door sales and tech sales, emphasizing the “grit advantage” that field experience brings to SDRs. “When you’ve faced a hard ‘no’ in person, a cold call feels like nothing in comparison,” he says. Changing SDR-AE Dynamics: Troy sheds light on how SDRs today are siloed from AEs, creating inefficiencies and reducing the perceived value of the SDR role. He argues, “SDRs should be incentivized on closed revenue, not just meetings scheduled. If SDRs aren’t setting up closeable pipeline, the model is broken.” Leveraging Tech Without Replacing the Human Element: Troy warns SDRs not to rely too heavily on automation, as it threatens their job security. “If you use tools to replace what makes you unique as a salesperson, human SDRs will no longer exist.” Career Pathing and SDR Motivation: Troy believes in promoting from within but stresses performance as the primary driver. For SDRs looking to move up, he advises a proactive approach: “Crush it at your current role, then ask to close smaller deals once you hit target—this shows you’re ready for AE responsibilities.” Insightful Quotes from Troy Barter: “Door-to-door sales taught me grit in a way tech never could. When you’ve walked a block in August Florida heat, SDR calls are nothing.” “You don’t bring Tom Brady in to block—you bring him in to win. AEs should close, not prospect; SDRs should build closeable pipeline, not just book meetings.” “SDRs, don’t let automation do your whole job. Those tools are here to help, but if they replace your role, you’ll be out of a job before you know it.” “If your SDR pipeline isn’t closing, your model is broken. Either the product doesn’t work, or the process is flawed—fix it.” “The tech hasn’t changed; it’s the mindset. The SDRs with the willingness to put in real work are standing out more than ever.” Episode Takeaways: Resilience is key in sales development: SDRs with door-to-door or other tough sales backgrounds have a built-in advantage. Real alignment between SDRs and AEs drives pipeline success. The current model, which separates SDR and AE goals, is hurting the industry. Career growth in sales development depends on demonstrating consistent success in pipeline generation, not just meeting quotas. Tools are just that—tools: The real value of SDRs lies in their ability to connect and problem-solve in ways automation cannot replace.

In this episode of Bold Calling, presented by Orum, Adam Sockel sits down with Joe Fontana, the North American Sales Director for BuyerForesight, for a dynamic discussion on building high-performing sales teams, the importance of sales and marketing alignment, and how discipline plays a key role in sales success. With decades of experience in both leading and consulting for sales teams across a variety of industries, Joe brings a wealth of insights into the often-overlooked fundamentals of sales—human connection and discipline. Key Takeaways from the Episode: The Power of Simplicity in Sales and Marketing Alignment One of Joe's biggest lessons throughout his career is the necessity of simple, clear communication between sales and marketing teams. He stresses, “Talk to me like I’m five until I tell you to stop.” By starting with the basics, Joe believes sales teams can understand the nuances of what marketing is doing and align on a cohesive strategy. According to Joe, salespeople should leave their ego at the door and focus on the common goal: reaching the right customers effectively. Building Relationships Before the Pitch When it comes to prospecting, Joe advocates for an authentic, relationship-first approach. Whether it’s at executive dinners or during one-on-one interactions, Joe emphasizes the importance of earning the right to pitch. He says, “You can’t put a price on human interaction and authenticity because that’s all sales is—just a series of conversations between someone who has a problem and someone who can solve it.” Sales Teams Must Learn Discipline and Structure Joe also highlights the importance of personal discipline, noting how his military background has shaped his structured approach to daily routines. He stresses the need for sellers to not only be well-prepared but also manage their time with intention. “I need to be disciplined and I need to be structured. I’m up every morning before 4:30 AM because I know that keeps me mentally sharp.” Solving for Misalignment in Sales and Marketing One of the most frustrating challenges for Joe is when sales teams don’t take full advantage of the high-quality prospects that marketing delivers. He shares how he often finds marketers frustrated by sales reps who don’t fully understand their ICP or don’t utilize the materials they’re given. His advice? Sales teams need to start seeing marketing as a valuable partner rather than an obstacle. Why You Should Listen: Joe Fontana brings real talk to the table, offering a candid view of what really works in sales development, pipeline building, and team collaboration. With practical advice for both sales leaders and individual contributors, this episode is a must-listen for anyone who wants to learn how to build a sustainable and scalable sales team. Whether you’re struggling with sales and marketing alignment or looking for ways to improve your personal sales discipline, Joe’s insights will leave you with plenty to think about—and implement. Quotes from the Episode: “You have to keep your ego at the door when building a sales org. You may think you know everything, but a day in the trenches will show you otherwise.” – Joe Fontana “Nobody wants to talk about your product. They’re not there for your brand. They’re there because of the challenge that keeps them up at 2 AM. Talk to that.” – Joe Fontana “If you can’t communicate with your colleagues in sales and marketing, how can you be relied upon to communicate with a prospect?” – Joe Fontana Connect with Joe Fontana: LinkedIn: Joe Fontana Subscribe & Follow Us: Stay up to date with future episodes of Bold Calling by subscribing on your favorite podcast platform!

In this episode of Bold Calling, Adam Sockel is joined by Leslie Venetz to dive deep into sales development strategies for 2025, backed by insights from Orum’s second annual State of Sales Development report. Leslie, with her years of expertise in sales, shares actionable advice on improving outbound strategies, reducing customer acquisition costs (CAC), and shortening sales cycles. Leslie stresses the importance of an omnichannel approach to outbound sales, explaining how a multi-touch, multi-channel, and multi-media strategy is essential to meeting prospects where they are. The episode also breaks down some of the key findings from the report, including the rising use of social channels and video in sales outreach. Throughout the conversation, Leslie challenges outdated sales norms, such as spending excessive time researching individual prospects, and offers a fresh perspective on AI’s role in the future of sales development. She advocates for AI as a tool to assist, not replace, salespeople, urging organizations to leverage AI for automating low-value tasks while keeping the human touch at the forefront. This episode is a goldmine for sales leaders looking to optimize their teams for the challenges of 2025, from balancing the roles of sales, marketing, and customer success, to creating more personalized and effective outbound strategies. Key Discussion Points: [02:06] The shift toward an omnichannel outbound strategy: Leslie explains the need for a multi-touch, multi-channel approach. [03:16] The myth of "quality vs. quantity" in outbound sales: Leslie challenges the notion that you must choose between personalization and scale. [05:55] Understanding your ICP (Ideal Customer Profile): Why aligning your strategy to your buyer’s behavior is crucial for outbound success. [06:15] How voicemails still play a powerful role in outbound efforts: Leslie outlines how a voicemail strategy can improve overall engagement. [10:03] Looking ahead to 2025: How organizations should rethink their approach to sales and customer retention to reduce churn and grow. [13:20] Collaborating with customer success (CS) for long-term sales success: Leslie discusses how outbound teams can better partner with CS to drive referrals and upsell opportunities. [17:07] Crafting effective sales messaging: Leslie shares why most outbound messages miss the mark and how to fix them. [33:14] AI’s role in sales development: Leslie emphasizes AI as an assistive tool that should help sales reps focus on higher-value tasks. [37:57] Leslie’s top 3 outbound channels: The non-negotiables for any sales development team going forward. Quotes: “To optimize outbound, you need to take a multi-touch, multi-channel, multi-media approach... The more diverse your outreach, the more likely you’ll reach your prospects where they want to be communicated with.” – Leslie Venetz “Most of your messaging sucks because it’s not customer-centric. Audit your copy to remove ‘I’ and ‘we’ language and replace it with customer benefits.” – Leslie Venetz “AI is assistive, not replaceive. Use it to automate low-risk, low-value tasks and free up time for building relationships.” – Leslie Venetz Resources Mentioned: Orum’s Second Annual State of Sales Development Report Sales Led GTM Agency Connect with Leslie Venetz: LinkedIn: Leslie Venetz Connect with Orum: Website: Orum

In this episode of Bold Calling, presented by Orum, we sit down with Charles Needham, Manager of Revenue Operations and Business Development at Fetch. Charles shares his fascinating journey from Wall Street and private equity to leading sales development teams. He explains how his background in economics gives him a unique lens through which he approaches sales, helping his teams become more efficient and strategic in their outreach efforts. Charles breaks down the role of risk in sales development, challenging the traditional focus on relationship-building. He argues that reducing uncertainty is key in today’s high-interest, high-risk environment. Charles also dives into how sales strategies must adapt to larger economic cycles, particularly focusing on efficiency and profitability over sheer volume-based tactics. Join us as we explore the future of sales development, the importance of channel-validated outreach, and how tools like Orum are helping sales teams scale while improving outcomes. Whether in sales, operations, or leadership, this episode is packed with valuable insights to help you rethink your approach to modern sales.

In this episode of Bold Calling, Adam Sockel is joined by Michael Pedone, founder of SalesBuzz, to discuss his incredible journey from being a commission-only sales rep to building a seven-figure business. Michael shares his insights into the importance of self-investment, overcoming cold calling reluctance, and why most salespeople don’t invest in their own development. Whether you’re new to sales or a seasoned professional, this conversation offers valuable takeaways on mastering the fundamentals and scaling your sales success. Key Takeaways: Michael's Sales Journey: From growing up poor with no college education to selling his first company for seven figures, Michael’s story is a testament to how dedication and continual learning can lead to success in sales. Overcoming Call Reluctance: Michael offers practical tips for conquering the fear of cold calling, emphasizing the importance of following a simple process. As he explains, “You just need to learn what to say, how to say it, and when to say it.” The Reluctance to Invest in Personal Development: Michael touches on a frustrating reality—many sales professionals refuse to invest in their own growth. He believes the key to long-term success lies in a willingness to learn and invest in yourself.

We've previously discussed how sales is a mix of science and art with Dee Acosta, but it's also equal parts freestyle and structure. It's "Yes, and" with just a bit of A/B testing. Shaheem Alam has big thoughts on why outbound sequence order doesn't matter and even bigger thoughts on why you need to pick up the phone.  In this discussion, Shaheem and Adam get nerdy about relevance and curiosity while focusing on where sales leaders need to be more rigid and where they need to allow some flexibility within the sales process.  Check out https://fiveringsmarketing.com/ to learn about their business and connect with Shaheem on LinkedIn. 

Chris Cicconi works with multiple organizations as a fractional sales leader, which has given him a nuanced understanding of revenue teams' minds. It takes a long time to earn trust, especially in a space where leaders and individual contributors are judged on their latest accomplishments and numbers.  Contrary to popular belief on platforms like LinkedIn, process change in sales takes time. It takes a concerted effort and willingness to be bold, especially when working with founders and early-stage start-ups. Chris and Adam discuss how creating that genuine change from a tactical standpoint and a 20,000-foot mindset shift.

"Too much can mean not doing as well." Will Aitken shares this truth with host Adam Sockel when breaking down his biggest challenge- Taking on too many opportunities. A talented sales professional who found a knack for creating video content that other sellers connected with, Will has spent this year branching out on his own. While this has created endless potential partnerships and opportunities to work with creative brands and people, the biggest struggle for Will is what happens when he says "Yes" too often. The conversation blossoms out from there, diving into Will's career as a content creator and seller, Adam and Will going deep on the importance of building trust during the sales process, and Will's endless love of cold calling. Looking for more information on Will's work? Check out https://willaitken.com/. And visit https://www.orum.com/podcasts to view every episode of the Bold Calling podcast.