Authentic Sales Leader Max Tipton on overcoming self-doubt as a sales leader

"The younger generation screams for authenticity."

Authenticity has become a critical word in not just sales, but all of business.

But what does it mean to be an authentic seller?

How are sellers of the past different from the sellers of today?

And how do you lead a team of today's sellers to become not just good, or great, or even exceptional, but elite?

Michael Norton is our first guest in the second season of the Authentic Sales Leader Podcast. Michael has seen and done it all in his near 40-year career in sales. Starting his sales journey under the legendary Zig Ziglar, he has seen trends come and go and has a keen eye for how the future of sales will shape up.

This episode, Michael talks to Amarpreet Kalkat about:

1. What it means to be truly authentic
2. How sales leaders should handle a multi-generational workforce
3. The relationship between effort and success
4. How to do all this and still have fun!

Welcome to the Authentic Sales Leader podcast, where exceptional sales leaders share stories, experiences, and advice on what it means to be an authentic sales leader. In this episode, we have Mallorie Maranda, VP of Sales at WorkRamp, joining as a special guest. Mallorie shares her journey from being an individual contributor to reaching the position of VP of Sales. She shares insights on the challenges and rewards of transitioning into sales leadership roles and provides valuable advice for those aspiring to become sales leaders.

Mallorie's career in sales began as an outbound BDR at Oracle. She started right out of college with no prior knowledge of sales or software. Her journey from an IC to a frontline manager was a significant step in her career. Mallorie emphasizes the importance of understanding all aspects of frontline sales management beyond coaching reps. Building territories, headcount planning, cross-functional collaboration, and pipeline acceleration are all integral parts of the role.

The transition from frontline manager to VP of Sales was a significant change for Mallorie. With this promotion came a loss of control over deals and forecasts, requiring trust and alignment with the leadership team. Time management also became crucial, as she had to prioritize the needs of different departments. Mallorie views these inflection points as opportunities for growth and development, shaping her skills and approach to leadership.

One key factor Mallorie highlights in her journey is the importance of continuous learning. She advises aspiring sales leaders to be like sponges, observing and learning from experienced leaders in their organization. This includes not only watching sales leaders but also leaders from other departments to gain a broader perspective. Seeking out mentors and forming partnerships with managers who are in the desired role can provide invaluable guidance and insights.

In terms of managing expectations, Mallorie shares her approach to setting clear expectations with her sales team. She believes that to keep reps motivated and engaged, it is crucial to explicitly communicate what is expected of them in addition to quota attainment. By providing weekly, monthly, and quarterly metrics, sales leaders can help reps understand what activities will give them the best chance of success. For Mallorie, controlling one's own destiny and focusing on low-hanging fruit are critical aspects of achieving success in sales.

Addressing the challenging times in SaaS sales, Mallorie acknowledges the low quota attainment rates and the need to keep reps motivated and excited. While adjustments to quotas can be a potential solution, Mallorie emphasizes the importance of maintaining consistency and avoiding setting the expectation that quotas will be adjusted whenever there is an economic slowdown. Instead, she focuses on providing guidance, setting clear expectations, and recognizing other scores on the rate card that indicate success as an AE within the organization.

Defining and fostering the culture within a sales organization is another essential aspect of sales leadership. Mallorie suggests tying the culture back to the company values and actively incorporating those values into daily operations. For example, at WorkRamp, two core values, "One Team" and "Always Be Improving," are emphasized within the sales organization. These values are repeated in meetings, shout-outs, and newsletters, providing consistent reinforcement. Additionally, WorkRamp has created a fun and engaging prospecting activity called the "Great Work Ramp Bake Off," where the entire AE team meets every Monday for 2 hours to prospect together. This activity encourages productivity while creating a sense of camaraderie and belonging.

When discussing the role of AI in sales, Mallorie acknowledges its inevitability and highlights its current benefits in terms of efficiency gains. Leveraging AI in tools like Gong Atrium has enabled sales leaders to be more efficient with their time by summarizing calls and providing actionable next steps. She also predicts that AI will play a significant role in lead qualification, prioritization, and self-serve models. Mallorie believes that as transactional sales become more automated through AI, sales teams will shift their focus to larger, more complex deals where the human touch and negotiation skills are essential.

In conclusion, Mallorie Maranda's journey to becoming a VP of Sales teaches valuable lessons about the path to sales leadership. Her advice on observing and learning from experienced leaders, setting clear expectations, fostering a positive and engaging culture, and embracing the role of AI in sales provides valuable insights for aspiring sales leaders. As sales organizations continue to evolve, the qualities of authenticity and continuous learning will remain fundamental for successful sales leaders in the ever-changing landscape of sales.

Welcome to the Authentic Sales Leader podcast, where we bring on exceptional sales leaders to dig into their stories and experiences, get their advice, and most importantly, learn what it means to them to be an authentic sales leader. In this episode, our host Jeff Kirchick is joined by Steph Sanders, the Head of Sales for the Americas at ContractBook. Steph discusses her background in sales, her role at ContractBook, and the challenges of building the go-to-market strategy for a European company in the United States. Additionally, she shares insights on hiring for sales roles, managing in a challenging sales environment, and the impact of artificial intelligence (AI) on sales.

## Background and Role

Steph Sanders has been in sales her entire career, graduating from college in 2009. She started working for a company that provided outsourced business development (biz dev) services for companies. She fell in love with the sales process and sales training and has since worked in various sales leadership roles in the software tech industry. Currently, she is the Head of Sales for the Americas at ContractBook, a Danish-based company, where she is responsible for managing the revenue function for North America and helping the company scale and go to market in the United States.

## Challenges of Building Go-to-Market Strategy

Steph has experience with European companies expanding into the US market and acknowledges that there are both pros and cons to this endeavor. One of the pros is that an established European company already has a playbook and go-to-market strategy for its home region, providing a sense of security. Additionally, being backed by prominent US-based venture capitalists (VCs) adds credibility and support in the US market. However, there are challenges, including cultural differences and time zone disparities. Steph highlights the importance of fostering unity within the company and facilitating open communication to minimize these challenges. Monthly town halls, meetups, and team-building activities are some of the strategies used to bridge the gap between the European and American teams.

## Hiring for Sales Roles

As a sales leader, one of the critical aspects of the job is building a strong sales team. When hiring, Steph looks for individuals who possess hunger, grit, and a strong work ethic. She focuses on candidates' stories and experiences, particularly those that demonstrate commitment and dedication, which are essential qualities for success in a startup or scale-up environment. Steph also values coachability and the ability to work well within a diverse team. She emphasizes using situational and behavioral questions to assess candidates' suitability and to gauge their personality and interpersonal skills, as these are crucial for building connections and rapport with clients.

## Managing in a Challenging Sales Environment

Sales professionals are currently facing unique challenges, with a downturn in the SaaS world and a decrease in hitting quotas. Steph acknowledges the difficulty this presents for sales managers, as it affects the team's morale and motivation. To address these challenges, she emphasizes the importance of transparency and empathy. Communicating openly about the situation and being transparent about the company's goals and numbers is crucial in alleviating uncertainty and doubt. Steph spends more time working on deals with her team to gain a deeper understanding of the sales process and to provide support. Additionally, she acknowledges the possibility of adjusting goals and compensation plans to align with the changing landscape and provide the team with a sense of support and solidarity.

## The Impact of Artificial Intelligence (AI) on Sales

AI is revolutionizing various industries, including sales. While many tools and technologies claim to automate salespeople's work, Steph believes that AI cannot replace the human element of sales. Instead, it can augment and support sales teams. Experimenting with AI tools for tasks like list building and prospecting research can help streamline processes and provide valuable insights. However, Steph emphasizes the need for sales professionals to embrace AI creatively and find ways to differentiate themselves from the competition. Simply replicating what others are doing with AI won't lead to success. Understanding buyer personality data and utilizing AI tools to personalize messaging and make data-driven decisions can be valuable in keeping up with the evolving sales landscape.

## Conclusion

Authentic sales leadership plays a crucial role in building and scaling sales teams. Steph Sanders emphasizes transparency, empathy, and open communication as essential qualities of effective sales leaders. Hiring individuals with hunger, grit, and coachability is vital for success in a startup or scale-up environment. Sales managers must adapt to challenging sales environments by being transparent about goals and compensations, providing support, and working together with the team to overcome obstacles. While AI has the potential to enhance sales processes, it cannot replace the human touch in sales. Sales professionals must embrace AI creatively and use it as a tool to stand out from the competition. By embracing authenticity and leveraging the power of technology, sales leaders can build successful sales teams and drive growth in the ever-evolving sales landscape.

## The Power of Transparency in Sales

Welcome to the Authentic Sales Leader podcast, where we bring on exceptional sales leaders to dig into their stories and experiences. In today's episode, we have a very special guest, Todd Caponi, a former sales leader, author, and keynote speaker. Todd is known for his work on transparency in sales and how it can revolutionize the industry.

## The Background

Todd shares his journey in sales and how his passion for coaching and leading led him to his current work. He reveals that his interest in decision science and learning theory led him down the path of writing books and coaching sales teams. Todd's fascination with the power of transparency in sales started with a research study he conducted while working as the Chief Revenue Officer of a company called Power Reviews.

## The Power of Transparency

Todd discovered that buyers today are more informed than ever before. They often read negative reviews first and prefer products with an average review score between 4.2 and 4.5. This insight prompted Todd to realize that our brains as human beings are drawn to the negative because we know that perfection does not exist. Transparency, therefore, plays a crucial role in building trust with customers.

## The Relationship Between Transparency and Authenticity

The conversation then shifts to the relationship between transparency and authenticity. Todd explains that while they are related, they are not the same. Authenticity is about being a human being and understanding that the customer's outcomes matter. Transparency, on the other hand, is about helping the customer predict and being honest about what your solution may not be able to provide. Both are vital in creating trust and building strong relationships.

## The Importance of Transparency in Sales Today

With buyers having access to more information than ever before, Todd emphasizes that transparency is essential in today's sales profession. Customers can easily find the truth about a product or service, so it's better for salespeople to be upfront and address any potential concerns early on. By embracing transparency, sales cycles can speed up, win rates can improve, and it becomes harder for competitors to undermine your messaging.

## Stories of Transparency in Action

Todd shares two powerful stories that illustrate the impact of transparency in sales. In the first story, he recounts a meeting with a potential client where he chose to start by highlighting the strengths of their competitor. This approach shifted the dynamic of the conversation, leading to a more collaborative and open discussion. In the end, Todd's transparency helped secure the deal.

In the second story, Todd discusses a workshop he conducted where he encouraged participants to embrace transparency. One attendee resisted the idea, believing that in the current economy, every opportunity must be pursued aggressively. Todd challenged this perspective, explaining that playing the long game and focusing on customer outcomes leads to better results in the short term as well.

## Implementing Transparency in Sales

To implement transparency in sales, Todd offers some actionable steps. First, sales professionals should reflect on their own buying behavior and recognize the power of negative reviews. Second, they should research their company's online reputation by searching their company name plus "reviews" on Google. This will provide insights into what customers are finding and how it aligns with their messaging. Lastly, leaders should embrace losses and analyze why deals were lost to uncover trends and improve messaging.

In conclusion, transparency is more critical than ever in sales. By embracing transparency and authenticity, sales professionals can build trust, speed up sales cycles, improve win rates, and differentiate themselves from the competition. Through stories and actionable steps, Todd Caponi demonstrates the power of transparency and invites sales leaders to transform their approach for greater success.

In this episode, we are joined by Ray Drew, the managing business development officer for Fund-Ex Solutions Group. Ray is considered a thought leader in the SBA lending space and also hosts the Art of SBA Lending podcast. In this episode, we will dive into Ray's background, the concept of SBA lending, his success in the industry, and his unique approach to differentiation and personal branding.

Ray's journey in the financial services industry began after he completed his marketing degree in college. Initially, he had no intention of pursuing a career in sales, but a marketing internship at an SBA lender opened his eyes to the world of small business lending. He quickly fell in love with both SBA lending and sales. Ray attributes a significant part of his success to the habit of reading books. In his early years, he read multiple books on sales and marketing, constantly seeking ways to improve his skills and knowledge.

SBA lending, according to Ray, involves lending money to small business owners for various purposes such as buying businesses, buying out partners, or purchasing real estate for their businesses. It is a niche industry but plays a vital role, especially in the M&A activity happening in the business world today. SBA loans can finance transactions up to $5 million, making them attractive to small to medium-sized businesses.

When it comes to differentiating himself from other SBA lenders, Ray emphasizes the importance of personal branding and education. By establishing himself as a thought leader through his podcast and YouTube channel, Ray has not only gained a following but has also built trust and credibility in the industry. His content provides valuable information that helps potential borrowers and referral sources understand the complexities of SBA lending. Ray believes that customers today have the power to do their own research, and by offering educational content, he is able to stand out from the competition.

As a player-coach, Ray also shares his insights and strategies with his team. He believes in hiring high-performing individuals who do not require excessive coaching. He encourages his team members to establish themselves as thought leaders and provides them with the freedom to explore their own growth paths. Ray's approach to leadership focuses on empowering his team rather than micromanaging their every move.

Referrals play a significant role in the SBA lending space, and while many professionals shy away from asking for referrals, Ray sees the value in it. He suggests asking for referrals at appropriate moments, such as when a problem has been solved for a customer or during the closing of a deal. By highlighting the positive outcomes and emphasizing the value they provided, SBA lenders can position themselves as trusted resources for potential referrals.

Ultimately, success stories for Ray come from helping individuals achieve their dreams of business ownership. He shared a heartwarming story of a receptionist who worked her way up to become a manager and eventually purchased the salon she worked at. These stories showcase the impact SBA lending can have on individuals' lives and solidify Ray's satisfaction in his career choice.

In conclusion, Ray Drew's journey in the SBA lending industry, coupled with his focus on personal branding and education, has propelled him to become a thought leader and successful sales professional. By sharing his knowledge and experiences through his podcast and other platforms, he has been able to differentiate himself and build a strong reputation in the industry. Ray's approach to leadership and his commitment to empowering his team further contribute to his success. Through his stories and insights, we can all learn valuable lessons about authenticity and success in the sales industry.

If you enjoyed this episode, make sure to check out the Authentic Sales Leader podcast and share it with others who may find it valuable. Remember, success comes not just from sales skills, but also from being authentic and providing value to customers and the industry as a whole.

# The Journey from Account Executive to VP of Sales: Insights from Max Tipton

Are you an aspiring sales leader looking for guidance and inspiration? Look no further! In this episode of the Authentic Sales Leader podcast, host Jeff Kirchick interviews Max Tipton, the VP of Sales at Paperless Parts, a fast-growing tech company based in Boston. Max shares his journey from being an Account Executive (AE) to becoming a successful sales leader. His story is filled with valuable insights and practical advice for anyone looking to make a similar transition. So, grab a notebook and a pen and get ready to learn!

Max Tipton's journey from AE to VP of Sales was not without its challenges. As he reflects on his transition, Max highlights the importance of having a growth mindset and being open to new opportunities. He attributes his success to the mentorship and guidance he received from Mike Stankus, who he considers the "Bill Belichick of sales." Mike instilled in Max the fundamentals of sales and held him accountable for results, which laid the foundation for his future leadership role.

One of the key takeaways from Max's journey is the importance of curiosity and tenacity in sales. He emphasizes the value of asking questions and understanding why things work the way they do. Curiosity helps sales professionals gain insights and knowledge that can be instrumental in their roles. Additionally, tenacity is crucial for salespeople who are passionate about their work and willing to go the extra mile to achieve their goals.

Max also highlights the significance of authenticity in sales leadership. He believes that great sales leaders bring energy, confidence, and a genuine desire to help their team succeed. They inspire and motivate their team members, even when they may not believe in themselves. Authentic sales leaders also excel in explaining the "why" behind decisions, fostering buy-in and alignment within the team.

In terms of sales hiring, Max looks for candidates who demonstrate curiosity and tenacity. He values individuals who ask meaningful questions and have a genuine interest in the problems their organization is solving. During the hiring process, Max assesses candidates' research and preparation, ensuring that they have a solid understanding of the company and the industry. This attention to detail helps filter out candidates who are not genuinely interested, resulting in a more qualified pool of applicants.

When it comes to being a good leader, Max believes that energy and confidence are vital. Sales leaders should inspire their team members to believe in themselves and their ability to accomplish challenging goals. Additionally, explaining the "why" behind decisions and fostering authenticity within the team are key attributes of a great sales leader. Building mutual respect and trust allows the team to collaborate more effectively and achieve better outcomes.

Max also discusses the impact of artificial intelligence (AI) on the sales community. He highlights the benefits of AI tools such as Chat GPT and Bard in enhancing sales go-to-market strategies. These tools assist sales professionals in gathering data, analyzing trends, and optimizing their processes. Max envisions a future where organizations have their own AI solutions that tap into internal data and provide valuable insights for driving revenue.

Finally, Max addresses the challenge of knowing when to walk away from a deal. He emphasizes the importance of having a well-defined Ideal Customer Profile (ICP) and qualification criteria. By setting clear boundaries and understanding the cost of inaction for the customer, sales professionals can identify the right opportunities to pursue. It's crucial to avoid investing too much time and effort in deals that are unlikely to close, allowing salespeople to focus on high-potential opportunities instead.

Max Tipton's journey from AE to VP of Sales provides valuable lessons for anyone looking to pursue a career in sales leadership. His emphasis on curiosity, tenacity, authenticity, and effective leadership resonates with aspiring sales leaders. By embracing these qualities, seeking mentorship, and leveraging AI tools, sales professionals can navigate their careers successfully and achieve their goals.

Are you ready to embrace the journey and become an authentic sales leader? Take inspiration from Max Tipton and embark on your own path to success!

Join host Jeff Kirchick as he interviews Brian Lamanna, a senior mid market account executive at Gong. In this episode, Brian shares his story of how he built his personal brand as a sales professional through authentic storytelling and engagement on LinkedIn. He discusses the importance of adding value, staying consistent, and being genuine in his interactions with the sales community. Brian also offers insights on the future of Conversational and Revenue Intelligence, the role of AI in sales, and how to successfully leverage technology while maintaining a human touch. 

**Background and Journey into Sales**
Brian Lamanna, originally from Chicago, attended Indiana University with a focus on business. Originally a marketing major, Brian made a pivot into sales after attending a sales workshop at his fraternity. Intrigued by the potential of sales, Brian interned at Anheuser-Busch and learned both the positive and negative aspects of sales. From there, he explored opportunities in the tech industry and eventually joined Gong two years ago. 

**Building a Personal Brand**
One of the highlights of Brian's career is his ability to build a strong personal brand through his engaging content and social media presence. He started posting on LinkedIn roughly a year ago, initially sharing company-related content. However, he soon realized the potential of sharing his own experiences and insights in sales. Brian's goal was to post once a week, gradually increasing the frequency, and engaging with others' content to build a network. Over time, his posts gained more traction, opening doors to new connections and opportunities.

**The Power of Authentic Storytelling**
Brian emphasizes the importance of authenticity in storytelling, especially in the sales process. He believes that automation and mass messaging cannot replace the genuine connection between salespeople and their prospects. Brian cites a specific example where he used authentic storytelling to address objections related to call recording. Drawing from his own experience of initially questioning the value of Gong's technology, Brian shared his personal journey and the positive outcomes he experienced. By connecting with his prospects on a human level, he was able to gain their trust and address their concerns effectively.

**The Future of Conversational Intelligence and AI in Sales**
As a sales professional in the conversational intelligence space, Brian discusses the rapidly evolving landscape and the rise of new competitors. However, he sees this increased competition as a positive sign, indicating the importance and potential of the industry. Brian envisions a future where sales tech tools, such as conversation intelligence, forecasting, and sales engagement, become integrated into one holistic platform. By streamlining these processes, sales reps can work more efficiently and effectively, ultimately closing more deals.

Additionally, Brian explores the role of artificial intelligence (AI) in sales. While AI can enhance sales efficiency by automating tasks such as call follow-ups and CRM updates, he urges sellers to strike a balance. Leveraging AI should not replace the human element in sales but rather complement it. Crafting personalized emails, conducting research on prospects, and sharing genuine stories are still vital components of successful sales strategies.

**Key Takeaways**
Brian Lamanna's insights emphasize the importance of authenticity in sales and personal branding. By sharing genuine stories, sales professionals can establish trust, address objections, and differentiate themselves in a competitive market. Building a personal brand through engaging content and leveraging social media platforms can open doors to new connections and career opportunities. Looking toward the future, the integration of sales tech tools and the careful use of AI will enhance efficiency and productivity for sales teams while still valuing human interaction and storytelling.

In conclusion, the journey of Brian Lamanna showcases the power of authenticity, personal branding, and leveraging technology in the sales industry. By following his example, sales professionals can navigate the evolving sales landscape, build stronger connections with prospects, and achieve long-term success as authentic sales leaders.

LinkedIn: https://www.linkedin.com/in/brianlamanna/
Jeff's ebook: https://www.amazon.in/Authentic-Selling-Principles-Sales-Everyday/dp/1735956902

Richard Harris is the founder of The Harris Consulting Group and co-founder of Surf and Sales, a one of a kind micro sales conference. He is the author of the ebook "Owning Your Job Search: Your step by step guide from application, to interview, to salary". 

He is also a 3x winner of the “Salesforce Sales Leader to Follow” award.

Richard Harris: On being Authentic and real

Richard Harris: On making content consistently

Richard Harris: On diversity in the field of AI and sales

Linkedin
https://www.linkedin.com/in/rharris415/

Ebook
https://www.amazon.com/Owning-Your-Job-Search-application-ebook/dp/B08TQHBVQF

Carson Heady is the Sales Director at Microsoft , an 8X CEO Award Winner, and a Best-Selling Author.

Being consistently ranked among the Top 20 Sales Gurus in the world is a testament to Carson's unrivaled expertise and influence in the sales industry. His impact extends to the realm of digital platforms as well, as he is ranked in the Top 50 Sales Authors on LinkedIn. 

Carson Heady: On what does it mean to be an Authentic Sales Leader

Carson Heady: On Social Selling

Carson Heady: On how selling has evolved

Linkedin

https://www.linkedin.com/in/carsonvheady/

Twitter

@cvheady007

Jeff Kirchick is the VP of Sales at Able. He has not only led a YC startup to a triumphant exit but also excelled as a sought-after speaker, sales consultant, coach, and investor. With a passion for empowering individuals, Jeff is also the mastermind behind impactful online courses and the author of the enlightening book, "Authentic Selling: How to Use the Principles of Sales in Everyday Life."

Going forward, Jeff will host the Authentic Sales Leader Podcast.

This is an excerpt from his talk from Humantic AI's Masterclass series where Jeff discusses various topics including accountability, detachment, and vulnerability, and challenges the notion that the customer is always right.

Jeff Kirchick: On what it means to be Authentic

Jeff Kirchick: On how accountability and authenticity are interrelated

Jeff Kirchick: On why vulnerability is important in sales

“So I encourage vulnerability. I encourage leaders to be honest about the things that they struggle with, with their team, not just sit up there and act like they're perfect and they're good at everything. You will garner much more respect and attention when people relate to you.”

Linkedin

https://www.linkedin.com/in/jeffkirchick/ 

Twitter

https://twitter.com/JeffreyKirchick?s=20

Check out his book
Authentic Selling: How to Use the Principles of Sales in Everyday Life 
https://www.amazon.in/Authentic-Selling-Principles-Sales-Everyday/dp/1735956902