Adapt and Thrive: Embracing AI and Authenticity in Modern Sales Leadership

When I started in sales over two decades ago, my toolkit was a phone, a notebook, and the sheer will to make 100 cold calls a day. Back then, hustle meant pounding the pavement and dialing until my fingers were numb. Fast forward to today: I’m leading sales teams at Microsoft in a world where artificial intelligence and social networks are as essential as a firm handshake. The game has changed – dramatically – but the core principles of sales success haven’t. This is the story of how I adapted from those early days to become a sales leader in the age of AI, and how embracing new tools without losing the human touch transformed my career.

I’ll be honest: at first, I resisted some of the changes. It’s easy to stick with what you know when you’ve had success. I remember years ago when LinkedIn started gaining traction for sellers – part of me wondered if posting content or sending connection requests could really move the needle. I was hitting my numbers on the phone; why rock the boat? But the truth was staring me in the face: the world was evolving, and if I didn’t evolve with it, I’d be left behind. Adapt or stagnate. There came a point in my career where I had to make a choice – cling to the old ways, or step into the future.

The New Reality of Sales – Change Is the Only Constant

One thing I’ve learned in my career: complacency is the enemy of success. Technology has always marched forward, and each wave changes how we connect with customers. I’ve seen it firsthand. In my early years, getting a “yes” meant relentless in-person networking and calls. Then came CRM systems, email, social media – each new tool initially met with skepticism, including from me. But every time I leaned into the change instead of away from it, I uncovered new opportunities.

Today, the buzz is all about AI in sales – predictive analytics, AI-driven research, even AI writing our first drafts. It’s easy to feel intimidated by it. I’ve watched some sales pros worry that AI will make them obsolete. I’ve also watched others – the adaptors and innovators – skyrocket their performance by using AI as an advantage. Here’s what I discovered: sales excellence is a moving target. What made you great last year might not be enough next year. The best sellers and leaders are perpetual students. They absorb new trends, test new strategies, and proactively reinvent themselves when needed.

I decided I would be one of those people. I embraced the mindset that if there’s a new tool or trend that can help me sell better or lead better, I want to know about it. That shift in attitude changed everything. Instead of fearing change, I started chasing it. When social selling emerged, I dove in and built a personal brand. When AI tools became available, I volunteered to pilot them on my team. I became an early adopter – and I quickly saw the payoff. My network grew exponentially. My win rates improved. I was learning faster than ever, because I wasn’t just reacting to change; I was running alongside it.

AI as an Ally (Not a Threat) to the Authentic Seller

One of the biggest turning points in my journey was realizing that AI isn’t here to replace salespeople – it’s here to empower us. A while back, I led a project where we experimented with an AI-powered sales assistant (our very own early version of a sales copilot). At first, some team members were skeptical – and honestly, I had my doubts too. Would relying on AI make our outreach feel robotic? Would it drain the humanity out of our customer relationships? These were valid concerns. After all, trust and rapport are the currency of sales, and you don’t build genuine trust with algorithms alone.

So we approached it intentionally. Rather than letting the AI run on autopilot, we used it to augment our human touch. For instance, the AI could analyze our CRM data and surface which customers might be ready for a new solution. It could draft a tailored email based on the customer’s industry and pain points – a task that might have taken me an hour of research and writing, the AI could do in minutes. But here’s the catch: we never sent anything without adding the human polish. I’d take that AI-drafted email and infuse my voice into it – referencing a client’s recent LinkedIn post, adding a personal anecdote, or injecting a bit of humor only a human would know to use. The result? I was reaching out more efficiently and more effectively.

Pretty soon I witnessed something amazing: using AI to handle the grunt work gave me more time to focus on what really matters in sales – the people. Instead of spending my evenings tediously researching, I could spend more time strategizing on how to solve a client’s business problem or simply having actual conversations with customers. AI became my 24/7 research assistant, my analytics guru, my content drafter – but I was the editor, the relationship-builder, the closer. The heavy lifting of data crunching and initial outreach templates was handled, and I could focus on listening to clients and crafting solutions.

The impact on my results was undeniable. By leveraging AI tools (like LinkedIn Sales Navigator insights and our internal AI systems) I was able to identify new opportunities faster than my competition. In one fiscal year, my team and I generated over $1 billion in revenue – a milestone I could hardly imagine back in my cold-calling days. In fact, embracing an AI-assisted, modern approach helped me become the #1 social seller in a company as large as Microsoft. But let me highlight something crucial: it wasn’t just because of the technology. It was because we used the technology to amplify the human element, not replace it. That’s the secret sauce. Every time I walk into a client meeting armed with AI-driven insights, my goal is not to wow them with data – it’s to show them I understand their needs and I’m here to help. The AI simply helps me do my homework better; the relationship and trust I build is 100% real and human.

These tools don’t replace you — they amplify you. At the end of the day, sales is still about people. AI can crunch numbers and suggest actions, but it’s your job to deliver empathy, creativity, and authenticity.

I often tell my team, imagine you’re a superhero. AI is like an exoskeleton that makes you stronger and faster – but your heart and mind are still in charge of the mission. When you view it that way, you stop fearing the tool and start appreciating what it can do for you. I personally moved from skepticism to advocacy. Now, I’m the one encouraging other sales folks: try this out, it can save you time, it can make your outreach smarter. But I also caution them: don’t you dare hit send on that AI-written email until you’ve made it sound like you.* Authenticity isn’t negotiable.

Building Your Brand and Relationships in a Digital World

Adapting to new technology was only part of the equation. Another huge leap in my career came from mastering social selling and personal branding. In a connected world, people don’t just buy products – they buy people. Your online presence can open or shut doors long before you ever speak to a prospect. Once I realized this, I went all-in on building a platform and a reputation that would make me impossible to ignore.

Let me take you back a few years: I was an unknown in the tech industry. I didn’t have an Ivy League MBA, I wasn’t a prodigy groomed for leadership, and I certainly wasn’t handed any free passes. How does a self-described underdog go from that starting point to leading major sales deals at Microsoft? By creating visibility and value through modern platforms. I started sharing my insights and stories on LinkedIn – not because anyone asked me to, but because I had experiences and lessons I knew could help others. I wrote about wins and failures, about deals and personal development, about the grind and the glory. I initiated conversations with industry leaders and chimed in on discussions that mattered to my customers. Essentially, I created a presence where previously there was none.

It wasn’t easy at first. I remember hosting my own little webinars and writing homegrown newsletters when virtually nobody was watching. I’d invite executives, partners, anyone who might find value. Sometimes only a handful of people showed up. Often, my posts would get only a few reactions. It would have been easy to quit, to conclude “this isn’t worth it.” But I kept at it, week after week, month after month, because I believed in the mission of helping others and building relationships. Slowly but surely, momentum built. A comment turned into a conversation, which turned into a coffee meeting, which turned into a multimillion-dollar deal. One introduction on LinkedIn snowballed into a network of hundreds of decision-makers. By sharing my voice, I inadvertently positioned myself as a trusted advisor in my space – someone who had ideas and solutions, not just something to sell.

That’s the power of social selling combined with authenticity. I wasn’t posting polished PR fluff; I was telling real stories from the trenches. I talked about times I failed and what I learned. I celebrated others’ successes more than my own. I made sure every piece of content had a purpose – either to inspire, educate, or solve a problem – never to just boast. Over time, people started to reach out to me. “I see how you’re doing things differently – can we chat?” They called me a “unicorn” – a quota-carrying sales leader who was also building a personal brand and helping others, which was (at the time) rare. Opportunities started knocking. I got invited to speak on podcasts, then to host my own. I met mentors, peers, even future hires through the content I was putting out. In short, by the time a prospective client was in a meeting with me, they often already knew who I was and what I stood for. That kind of trust and credibility is priceless in sales – and it came from daring to put myself out there and share real value publicly.

If you’re reading this and wondering whether you should bother posting on LinkedIn, or writing that article, or commenting on that industry discussion – let me assure you, it’s worth it. Personal branding isn’t just a buzzword; it’s how you scale yourself. It’s how you become more than just a name in someone’s Rolodex. It’s how you attract career opportunities and client inquiries that you didn’t even know were out there. In my case, writing a book and sharing content online literally changed the trajectory of my career – it got me noticed by leaders who opened doors I didn’t even know existed.

And here’s the beautiful synergy: the more I leveraged digital tools like LinkedIn to build relationships, the more effective my use of AI became, and vice versa. For example, I would post an article about a hot industry trend, and then use AI analytics to see which executives engaged with it – those insights became new leads for genuine conversations. The AI would help identify who in my network was showing interest, and my human side would then reach out with a friendly note: “Hey, thanks for commenting on my post – how’s your team approaching that challenge?” Many of those chats turned into trust-filled business relationships. It’s a one-two punch of modern selling: establish yourself as a trusted voice, and use technology to listen at scale.

Leadership in the Age of Innovation and Empathy

Climbing the ranks from front-line seller to sales leader taught me a crucial lesson: great sales leadership isn’t about managing numbers, it’s about inspiring people. And in an age of constant innovation, leading effectively means guiding your team through change with vision and empathy. As a leader, I’ve made it a priority to create a culture where experimentation is encouraged and failing forward is accepted. Why? Because if my team fears change or fears making mistakes, they’ll resist new ideas like using AI or leveraging social media. I openly share my own learning journey – how I fumbled the first time I tried something new, but kept going. When my team saw me, their leader, actively learning a new sales tech or vulnerably admitting that I didn’t have all the answers, it gave them permission to do the same.

In today’s environment, a leader must wear two hats: the innovator’s hat and the coach’s hat. With the innovator’s hat, you’re scanning the horizon for anything that could give your people an edge – new tools, new strategies, emerging market shifts. You’re not just reacting to the future, you’re preparing for it. With the coach’s hat, you’re focused on the timeless fundamentals – listening, advising, motivating, and sometimes giving tough love. Let me give an example: when AI tools started rolling out to our org, I didn’t mandate their use from on high and measure compliance. Instead, I sat down with my team and said, “Let’s play with this. How can it make your day easier? What problems could it solve for us?” We held hackathons and friendly competitions to see who could get the coolest result from our sales AI assistant. It turned learning into a game rather than a chore. And for those who were hesitant, I paired them with early adopters as buddies. Bit by bit, the fear gave way to curiosity, and curiosity led to mastery.

But leadership today also means keeping it real. All the high-tech tools in the world don’t mean a thing if your team doesn’t trust you or if they’re burnt out. I’ve never forgotten that under the quotas and dashboards, we’re all human beings with hopes, fears, and dreams. I make it a point to know my team members’ individual goals – not just their sales targets, but their career aspirations and what motivates them personally. That knowledge lets me align new initiatives (like learning a new AI platform) with what they care about. For instance, if I know someone on my team wants to rise in the organization, I might encourage them to take point as the “AI champion” for our group, giving them a chance to shine and grow their leadership skills. Another rep might be passionate about social causes, so I show them how building a personal brand can amplify the causes they care about while also helping their sales career. It’s all about connecting the new task or tool to an individual’s “why”.

And yes, authenticity plays a huge role in leadership, just as it does in selling. Gone are the days of the untouchable, always-perfect boss. I’ve shared stories of my own struggles openly – like the time early in my management career when I blew it with a major client through sheer overconfidence, and what I learned from that failure. I’ve written on LinkedIn about battling impostor syndrome and overcoming personal hardships. Far from diminishing my credibility, these admissions have strengthened it. My team knows that when I say “I’ve got your back,” I mean it, because I know what it’s like to stumble and get back up. Leadership with empathy and authenticity creates loyalty and trust – and trust, whether with your team or your customers, is the bedrock of any enduring success.

From Underdog to Sales Leader – Key Lessons Learned

So, how can you take all of this – the technology, the branding, the leadership approach – and apply it to your own journey starting today? I want to boil down some of the most impactful lessons and strategies that you can put into action right now. These are the principles that took me from a cold-calling underdog to a modern sales leader, and they can help you accelerate your own path:

Embrace New Tools, But Keep Your Voice: Don’t shy away from AI, CRM updates, or other tech innovations that can make you more effective. Do leverage AI to research prospects faster or draft outreach messages, but always infuse your personal touch before hitting send. Your genuine perspective and care are irreplaceable – use tech to enhance, not erase, that uniqueness.Be Consistently Curious and Adaptable: Treat every change as an opportunity to grow. Whether it’s a new market trend, a new sales methodology, or a shift in customer behavior, approach it with curiosity. Ask questions, seek training, experiment. The sellers who thrive are the ones who learn faster than the competition. Make “lifelong learner” your identity.Build Relationships Before You Need Them: In the digital age, your network is your net worth. Connect with people in your industry, engage with their content, offer help without immediate expectation of return. By the time you’re in a business negotiation or need a favor, it’s those authentic relationships forged over time that will set you apart. (I can’t tell you how many deals were won because a prospect already felt like they knew and trusted me from our online interactions.)Invest in Your Personal Brand: Take control of your narrative. Share your journey, insights, and successes in your own voice. Whether it’s writing an article, posting a video, or simply commenting thoughtfully on others’ posts – put yourself out there. Consistency is key; showing up regularly will keep you on your network’s radar. Over time, you’ll become the go-to person in your domain, and opportunities (jobs, clients, partnerships) will start coming to you.Lead with Empathy and Purpose: Whether or not you have a formal leadership title, lead by example. Demonstrate the behaviors and values you wish others would emulate. Help colleagues embrace new tools, mentor someone less experienced, share knowledge openly. When you lift others up and lead with a servant mindset, you become magnetic. People want to work with and buy from those who genuinely care. Plus, empathy will give you insights into your customers and team that no amount of data can provide.Stay Resilient and Resourceful: There will be setbacks – a deal gone sour, a post that gets no engagement, a quarter where nothing seems to go right. Trust me, I’ve lived through them. Use setbacks as fuel. If one approach fails, treat it as data and adjust. Maybe that big client said no – how can you leverage your network to get a warm introduction elsewhere? Maybe your team missed target – what new strategy or coaching can you deploy? No one is coming to hand you success; you have to navigate through challenges with grit. The good news is, every challenge overcome builds your confidence and capability.Keep Your Customer at the Center: Amidst all this talk of AI, personal branding, and strategy, never forget: at the end of the day, it’s about solving problems for your customer. Use every tool in your toolkit to understand their needs at a deep level. Show up for them. Listen more than you speak. When a customer senses that you truly have their best interest at heart – that you’re not just there to make a sale, but to make a difference for them – an incredible thing happens: you stop being just a vendor and become a trusted partner. And that’s when sales (and leadership) transcends transactions and turns into long-term relationships.Embracing the Future with Heart

As I wrap up this chapter of my story, I want you to remember one thing above all: the future of sales belongs to those who blend innovation with authenticity. I’ve shared how adapting to new technologies like AI and building a personal brand transformed my career, but I want to emphasize that none of it came at the expense of being human. In fact, it made being human more important than ever. By adapting and learning, I gained new superpowers – but by staying true to my values, I ensured those powers were used to genuinely connect and help others.

Looking back, the underdog kid from Missouri who started in a call center could never have imagined using algorithms and global networks to win deals. Yet, here I am – and if I could do it, so can you. My journey is proof that you can honor timeless principles – like trust, integrity, hard work – while also reinventing yourself and your approach for a new era. It’s not an either/or choice; embracing change and staying authentic is a both/and superpower.

The road ahead for all of us in the professional world will feature even more new tools and unexpected twists. You might be reading about some new AI breakthrough or platform every other week and thinking, “How do I keep up?” The answer: by staying grounded in what makes you you (your unique perspective, your story, your passion to serve) and being fearless in acquiring new skills. When you marry those two – your authentic self and a mindset of continuous adaptation – you become unstoppable.

I encourage you to take a look at your own career and ask: Am I adapting fast enough? Am I leveraging the incredible tools at my disposal and also investing in the relationships around me? Am I stepping out of my comfort zone regularly to learn something new? If not, make today that turning point. Start that passion project. Learn that new platform. Reach out to that mentor. Post that insight that’s been on your mind. The best salespeople and leaders I know are not the ones who never fear change – they’re the ones who feel that fear and move forward anyway, determined to lead the pack.

Every day, you have a choice to make: cling to what’s comfortable, or push yourself toward what’s possible. I chose the latter, and it made all the difference. My wish for you is that you choose to adapt and thrive, to lead with both head and heart, and to write your own extraordinary success story in this exciting new chapter of our professional world.

Now go make yourself impossible to ignore – I’ll be cheering you on from the sidelines, every step of the way.

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