In this episode of RevOps Champions, Brendon Dennewill welcomes Chris Briest, the founder of Mile High AI and a seasoned sales enablement leader, for an engaging discussion about the transformative power of AI in sales organizations. Chris shares his journey from SaaS enablement roles to launching his own consultancy, focusing on practical applications of AI rather than just theoretical potential. The conversation centers on how revenue leaders and individual sellers can leverage AI to differentiate themselves in a competitive market, stressing that the true winners will be those who adopt and effectively use these tools.
A major highlight of the episode is the exploration of personalized outreach at scale. Chris explains how AI, when properly equipped with brand and persona context, can enable reps to perform high-level research and generate tailored messaging faster than ever—reducing prospecting and multithreading time by up to 80%. He provides actionable advice and live demonstrations on integrating custom GPTs and context kits into workflows, making it clear that the goal is to empower reps and streamline processes, not just add another layer of technology. They also tackle the hurdles of change management and adoption, emphasizing the importance of embedding AI seamlessly into existing routines and investing in continuous training.
The conversation wraps up with a call to action for both sales leaders and individual reps. Senior leaders are urged to make decisive moves toward AI adoption, resisting the temptation to let change aversion stall progress, while reps are encouraged to invest in AI fluency as a way to advance their careers and become indispensable. Throughout the episode, Chris and Brendon’s insights provide a roadmap for mid-market and emerging companies to harness the operational and competitive advantages AI offers—driving more relevant outbound activity, stronger conversations, and ultimately greater revenue impact.
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About the Guest
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Chris Briest | Founder at Mile High AI With more than a decade of experience transforming sales enablement, Chris Briest shares how AI is reshaping go-to-market strategy. As the Founder of Mile High AI and former Revenue Enablement Leader at Freshworks, he has pioneered GPT-powered selling strategies that have driven a 32% increase in SAOs, slashed prospecting time by 80%, and boosted seller confidence by 45%. His work has equipped global teams with the tools to engage more effectively, scale outreach without additional headcount, and lead the way in AI-driven selling. |
Episode Transcript
Welcome and Introduction
Brendon Dennewill: You're listening to Brendon Dennewill, a podcast created for B2B leaders to help you align your people, streamline your processes, trust your data, and leverage technology in order to grow your business. Chris Briest, welcome to the show.
Chris Briest: Thank you for having me. Appreciate it.
Brendon Dennewill: How are you doing?
Chris Briest: Very well. Yourself?
Brendon Dennewill: Awesome. It's good to have you on, Chris. We were introduced by Mel, one of the rock stars on the team here at Denamico. Tell us a little bit about Mile High AI.
About Mile High AI
Chris Briest: Mile High AI is a consulting business I started about eight months ago. We're relatively new. I've been in the sales training space for my entire career, with AI as a real passion for the last two and a half years. Following my previous ventures in SaaS go-to-market, I locked onto AI, not just to talk about it, but to figure out how to make it work. My focus has been on application to sellers, helping individual reps and emerging companies figure out how to break off AI in manageable pieces. The example I often use: it's the old riddle of how do you eat an elephant? One bite at a time. A lot of people are looking at the AI elephant in the room and don't know where to take that first bite. The last couple of years have been a huge focus on helping people do exactly that.
The Struggles of Outbound Sales and the Personalization Gap
Brendon Dennewill: You alluded to some enablement leadership roles at a couple of well-known companies over the last five or six years. What did you learn there, and is there a link to what you're doing today?
Chris Briest: Big link. SaaS has been struggling for a while now, and when you look at the outbound motion and prospecting, that struggle has been building. Personalized outreach really underpins it all. We're very used to XDRs sending buyer-based persona messages to lists of contacts we don't really know, celebrating their funding round or noting they're in a new role. At the end of the day, that doesn't resonate. We're at a point where everyone expects a high degree of personalization. As soon as we don't sense it, our instincts kick in: "Was this written for me, or is this spray and pray?"
Companies still pushing that approach are going to keep facing those struggles. So one of my big focuses in AI application is: how do we scale personalized outreach? When I first started making that case, leaders would look at me wide-eyed. "We don't have time for that. We have to hit numbers." But when you have the right tools, the right process, and a team that's tactically enabled to execute, it's incredible what you can do. We were able to reduce prospecting and multithreading time by 80% on average. That's a massive increase in capacity, and the conversations that come out of it are meaningfully better.
Relevancy as the Foundation of Effective Outreach
Brendon Dennewill: From what you've learned over the last two and a half years, what is the key to personalized outreach for outbound sales reps?
Chris Briest: Relevancy. Relevancy is key. In a world full of busy inboxes, relevancy is your currency, and AI is how you earn it at scale. To be relevant at scale, you need the right toolset and, more importantly, AI fluency. A lot of people have dabbled with ChatGPT: rewriting an email, summarizing something. That's table stakes. That's where we were a couple of years ago.
The real shift is figuring out how to bring in relevant information: your go-to-market assets, persona cards, marketing messages, brand info, sales process. When you help your AI tool understand those things, it can give you a much crisper message that not only sounds like your brand but speaks directly to that persona. And it's not just about what we assume they care about. Within a couple of clicks, we can find out exactly what's happening at that company. What are the triggers? Maybe they missed numbers last quarter in a competitive market. When you combine that information with a deep understanding of your personas, that's the powerful message. That's what gets people willing to respond and have a real conversation.
Tools, Tactics, and the "Open World" Problem
Brendon Dennewill: Let's get into the approach. Say you're working with a company that has 25 outbound sales reps. What are you doing to enable them to achieve this kind of relevancy?
Chris Briest: It's a combination of tools and tactics. Businesses are buying AI, and I have plenty of conversations where they say, "We already have AI in our tech stack." My challenge to them is: what are you actually getting out of it? It might be pumping in data, intent signals, and contact information, which is great. I don't want people to give that up. But how well are reps actually leveraging it? Are we getting good messages and better conversion out of that information?
I want people to understand not just how to execute within any single AI tool, but how to bring all of these tools together so they don't feel disparate. The analogy I've been using: there's a new Grand Theft Auto coming out. It's open world. You can run around and do a lot, and that's most LLMs: they can do anything. But until you play the story or campaign and understand the through-line of the game, it's hard to adopt it and make it part of your daily routine.
So understanding how to make AI complementary to today's process and methodology is key. We're not replacing it, we're accelerating it. In my case, I build custom GPTs. I have a couple of free ones publicly available that have tens of thousands of uses across the globe in the last year. They work. I also build more bespoke custom tooling with additional capability behind the scenes. When you bring those two things together, that's when the lights start turning on for teams.
Who Chris Works With
Brendon Dennewill: Who are your ideal clients, and what sizes of business are you typically working with?
Chris Briest: The sweet spot right now is mid-market companies, especially tech companies in early to later-stage funding rounds. These are teams trying to do a lot with a little. They want to go fast and stay nimble, so AI is an easier conversation to have. With enterprises, it takes a lot to move things unless you have a vocal leader saying, "Let's do this now." Change and adaptation is a real challenge at that scale.
I talk a lot with GTM leaders, CROs, and heads of enablement. And while I focus heavily on sellers, my training background means I also see enormous value in what AI can do for onboarding, continuing education, message adoption, and making sure what's coming from the top is actually being seen and executed in the field.
The Most Common Challenges AI Can Solve
Brendon Dennewill: Is there a common theme in the challenges you're seeing? What are the one, two, or three most frequent problems that AI can realistically fix?
Chris Briest: Trying to do more with less is the big one. There haven't been major hiring sprees across the industry. Workforces have been reduced, and companies are trying to squeeze the most out of their existing teams. That 80% reduction in prospecting time I mentioned isn't just theoretical: it increases an individual rep's capacity by nearly three times. Theoretically, if you're able to make that many more calls and send that many more emails, the numbers alone will pay it off.
Beyond capacity, there's the challenge of personalization across a diverse buyer group. In tech, especially in IT, many stakeholders are involved in a purchase decision. How do we make sure our outbound is relevant to each of them? We need to give all of them a unique reason to come to the table, and then when we show up on that call, we need to have something unique to say to each of them.
That's especially hard for outbound teams because XDR roles have traditionally been filled by people earlier in their careers who haven't yet built that commercial acumen. They don't always know how to gather the right information, and it's intimidating. That's where the right tactics, tools, and process make a real difference. Generative AI lets you interact, ask questions, even do voice-to-voice roleplay. I couldn't have imagined a decade ago being able to practice talking to a CIO before actually talking to one. Getting to that first deal faster and having better stakeholder conversations: those are the things I consistently hear from everyone.
The Tech Stack: Supplements, Not Replacements
Brendon Dennewill: Let's dig into the tech stack a bit. Mid-market companies are already using a CRM. Are you adding tools that supplement it, or working within it?
Chris Briest: I'm AI agnostic. If a company has Gemini, Copilot, or ChatGPT Enterprise internally, I'm completely on board with that. But here's where I'll be a little audacious: even the CRM-embedded AI, the Outreach AI, the Gong intelligence, the Lavenders and Apollos and Clays of the world, all of them fall short in a couple of areas. Many will bring information in. Some will automate a first email. Some will bubble up an industry insight. But what every single one of them is lacking is a true end-to-end assistant that understands your brand, what you're selling, how you sell it, who you compete with, and can support you in using that data throughout the entire deal.
The other gap is that these tools stop at the first outreach message. What about getting ready for a discovery call? Being on the call? Debriefing it? Moving into demos, RFPs, negotiations? Our sales process doesn't end at the first email. So there's very little out there that looks at this holistically.
When I come in, my answer is: great, you have these other AIs. Here's the value they provide. Here's how we bring it all into one place, one assistant, that helps you work through the entire deal cycle. And even if a deal goes cold, that assistant is there waiting. When you get that callback six months later, you can pick right back up.
What a Custom GPT Sales Assistant Actually Is
Brendon Dennewill: For the more traditional folks listening, when you talk about an assistant, you're essentially describing an AI agent or a collection of agents. How would you explain it simply?
Chris Briest: In the example I'll show, it can simply be a custom GPT in ChatGPT. That's my LLM of choice because it's dynamic enough to do everything I need, unlike some others. When people hear "custom GPT," they often think it sounds complicated. I actually run free sessions called "Demystifying Custom GPTs for Sellers" because it's genuinely straightforward. Once you know where to start and how to give it a few helpful pieces of information, not just about yourself but about your brand, your value proposition, your competitive intel, those are the things that really uplevel your output and turn research into relevant messaging.
Brendon Dennewill: And when you set it up, you're also including your ICP. The more context you provide, the more helpful the assistant becomes.
Chris Briest: Exactly. I've been on a tear on LinkedIn lately about this: context is king. You don't like what you're getting out of AI? Look at what you're putting into it. Garbage in, garbage out. If you're not giving it the information you want it to know, you can't expect it to know it.
Live Demonstration: GPT-Powered Selling in Action
Brendon Dennewill: What would be most valuable for the revenue leaders, enablement leaders, or CX leaders listening? Is there anything else you'd like to share before we potentially look at the tool?
Chris Briest: For a lot of people, it starts with making the choice to go down this road. Understanding there's going to be a little investment, a little novelty. But you see instant results. Coming from a training background and having been through a million methodology trainings, I know the typical expectation: "We hope in six to eight weeks we see an uptick in conversion." With generative AI and the right tools, you start getting results immediately.
GPT Powered Selling, at gptpoweredselling.com, is my branded approach for how individuals and teams augment their selling with generative AI. One of the public tools I have out there is my SDR/BDR Sales Research GPT. It's built for anyone who's prospecting or needs to better understand a company and turn that information into action.
The first thing you'll notice is what I call a context kit. It's a simple text file containing the things I mentioned: my brand, my solution, how I solve problems, my flywheel zones, competitive intel. The same things you'd use to onboard a new rep are what you need to make your AI GPT-ready. These are assets you'd already be comfortable showing a customer. Nothing proprietary. And I know that's an immediate concern, especially for security teams. That's part of the training: we teach people what to share and what not to. But by consolidating that information and making it available as an attachment, you raise the quality of output by orders of magnitude.
So here I'll start with a simple prompt: "I want to sell my GPT-powered solution to Snowflake." What you see back immediately is what every seller is looking for: who is this company, what do they offer, where do they play, how do they make money. You're getting this faster than before. And I never expect reps to craft complex prompts. What I want is to offer the prompting infrastructure I've already built so reps can get this information quickly without having to think about it.
Where the value really starts to shine is not just pulling data, but tying that data to our solution. That comes from the brand kit. As I read through the research, I might notice Snowflake's expansion into India. That's potentially juicy: a company expanding globally will need to get new teams up and running fast and maximize market share. I dial in on that. I ask: "How do I use this to sell?" And what comes back are not generic ideas. These are ideas specifically aligned with my AI-powered workflow, how I enable new sellers, and how I scale messaging globally.
Pro tip: never ask ChatGPT to "write me an email." You've seen what that looks like. It doesn't sound like a human. What you want to become is a curator of messaging. Have a tool that gets you 70 to 80 to 90 percent of the way there and lets you make final adjustments. If you've built your context kit well and included customer stories, it will automatically tie them in. If it knows you increased a similar company's sales by 15% in a month, it's going to include that in your message.
The second tool I'll show is the 10K Analyzer. If you've ever looked at a 10-K, that's the annual financial disclosure. It's a big document but it's full of useful information: what's gone well, what hasn't, and forward-looking vision for the future. I've just attached Snowflake's recent 10-K. In about five seconds, it gives us a summary, identifies key initiatives that align best with my solution, even pulls a direct quote I can reference. It gives me specific angles for how and where I can add value, and how to say it on brand.
From there, I can spin up messaging for a CRO in minutes. If I have ten other contacts to reach, I paste in their LinkedIn profile or key details about their role. Rinse and repeat. In five to ten minutes, I can create multiple unique, persona-specific touch cadences. They all sound individualized, and most importantly, they sound like your best rep.
CRM Integration and the Vision for a Unified Assistant
Brendon Dennewill: What part of what you just showed us is being pulled back into the CRM?
Chris Briest: That's part of the hard reality of where we are in technology right now. What I just showed are my public tools, available to anyone. I do have proprietary tools I offer to companies, and we're working on productizing them and going to market this year. Once you move outside of ChatGPT, that's where those integrations to CRMs and other tools become possible. I've had conversations with a lot of CRM platforms. I've seen all the demos. They have the table stakes functionality, but they haven't thought far enough ahead about how to do what I showed, let alone how to look outside themselves and pull in external tools.
My five-year vision: there needs to be one ultimate assistant. Every tool has an "ask me anything" that's largely useless. Why should a rep have five separate AI interfaces across all their tools? You should have one assistant. You ask it anything, and through an agentic environment, it goes out to these sources: pulls your recent Gong call, grabs the latest contact details, reaches into your content management system for persona cards and competitive intel. All through simple natural language, or through what I call zero-prompt commands, where a single word or click moves you through the next step in the sales process.
We're not there yet. But right now, it's about understanding where this assistant lives, how information flows in, and how to take the best of it back out to update your CRM, prepare your decks, run your deal reviews, and look sharp in your QBRs. Eventually we'll get to that unified assistant. But the reps who are building that muscle now will be far ahead when we do.
Brendon Dennewill: Which is obviously very attractive to a lot of people.
Chris Briest: Absolutely.
The Mindset Shift: Revenue Leaders and Sales Reps
Brendon Dennewill: There are two roles that need to go through a mindset shift here: the revenue leader and the individual sales rep. What does that shift need to look like for each of them?
Chris Briest: For revenue leaders, bluntly: make the choice. That's it. There are tons of conversations about wanting to do it, but very few are saying, "Okay, let's do it. Let's make the investment and take the first step." I made a post recently about this: January 2nd was the midpoint of the year, and we are now closer to 2050 than we are to the year 2000. If that's not a call to action to make sure you're current with AI, I don't know what is. And if you don't make this change, your competition will make it before you.
For individual reps, it's about learning to use the tools effectively so you don't feel like they're slowing you down. I work with a number of individual sellers who see the writing on the wall and want to differentiate themselves. I've been saying this for over two years: very rarely is AI going to replace you outright, especially in sales. But the people who can use AI well, who can walk into an interview and say, "I can do more, I can move faster," those are the people who are going to stand out.
Brendon Dennewill: Those individual sellers are essentially investing in themselves and their futures. If the organization they're at doesn't come along, they become very marketable to any company that has already made the move.
Chris Briest: Exactly. And especially for a younger seller in a BD role trying to move into an account executive or strategic position: there's your differentiator. You have the tools to access the insights that tenured sellers carry in their heads, and you can access them faster and apply them more strategically.
Closing Advice for Mid-Market Leaders
Brendon Dennewill: Last question. Every C-suite leader is going to be impacted by this: the revenue leader, the CFO, the CEO, the COO. A statistic that keeps coming up is that 100% of leaders know AI is going to change their business, but only 5% are actually doing something about it. What's your final word of advice to mid-market leaders trying to figure out what to do next?
Chris Briest: Beyond just saying "do it," find a couple of low-hanging fruits and grab them. We get wide-eyed about all the possibilities, it becomes overwhelming, and suddenly it feels like too much. But there are quick wins available right now. What I showed today, doing fast research, turning it into relevant insights, turning that into persona-based messaging, you will have stronger conversations instantly. You will spend less time instantly.
Before you think about a full GTM transformation or AI-powered playbooks, get a couple of basic tools like these into the hands of your reps. Encourage utilization. Get frontline manager buy-in. Then sit back and watch. You'll see the results. You'll hear the conversations. And one of my favorite pieces of feedback from early adopters is customers saying outright: "You seem a little better researched than the other five reps I spoke to this week." That's powerful. You are relevant. You are a partner, not just another salesperson walking through the door.
That all starts with understanding how to break off just a small piece, use these tools, and become the most relevant person in the room.
Brendon Dennewill: That's a great place to wrap up. Chris, thanks so much for joining me today. What you've shared is going to be genuinely valuable to a lot of our listeners and audience. I look forward to watching this space with you over the coming months.
Chris Briest: Going to be an interesting time. Thanks for having me, Bren.
Brendon Dennewill: Take care, Chris.
Chris Briest: Cheers.
Brendon Dennewill: Thanks for listening to Brendon Dennewill. If today's episode gave you a new idea for scaling smarter, or helped you see your team, processes, or tech in a new light, be sure to subscribe so you don't miss the next insight. And if it hit home, share it with a colleague. Let's grow this community of forward-thinking leaders together.
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