The Sales Manager Development Playbook [Guide]
The Sales Manager Development Playbook:
15 Steps to Unlock Revenue Acceleration
[Guide]
Sales Leaders
What Type of Sales Manager Are You? (& How to Make It Your Superpower) [Webinar Recording]
What Type of Sales Manager Are You? (& How to Make It Your Superpower)
[Video Recording]
Your Sales Manager Survival Kit [Cheat Sheets]
Your Sales Manager Survival Kit
[Free Resources & Cheat Sheets]
How Tenured Sales Leaders Took Their Coaching to the Next Level
At Dun & Bradstreet, some of the most tenured sales managers, leaders with over 20 years of experience, had a breakthrough they didn’t see coming.
John Healy, one of our Sales Advisors, spent a full day with the team, leading a session on Driving Performance with Goals (a longtime manager favorite). But this wasn’t another pep talk about why goals matter. It was hands-on. Practical. Focused on building real connections between daily activities, KPIs, and long-term outcomes.
For many in the room, it was the first time the dots fully connected.
The real shift didn’t come from slides or lectures. It happened inside The Sales Bar by doing the work.
The managers rolled up their sleeves and practiced how to:
- Map goals to rep behaviors
- Build coaching cadences that actually stick
- Practice conversations before trying them live
- Lead like strategic managers, not just task supervisors
By the end of the day, those same leaders were mapping out new team strategies, role-playing coaching conversations, and sharing real-life examples of how they would start applying new approaches immediately.
They weren’t just talking about change. They were leading it.
Why did it work?
Because they didn’t just learn about managing performance. They experienced it.
The Sales Bar isn’t just another resource. It is where even the most experienced sales leaders go to sharpen their edge and lead with purpose.
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Best AI Tools, Tips, And Prompts For Sales Prospecting
If your reps are still using AI like it’s 2023 (or not using it at all), they’re already behind. In our Sales Shot, I sat down with four sales pros and AI enthusiasts whose teams are actually using AI for sales prospecting, not just talking about it. We’re talking AI-enhanced targeting and prospect research, coaching bots, live conversation sentiment tracking, even inbound AI voice agents that are outperforming humans (yes, really – so, will AI take over sales jobs? That’s a topic for another blog!)
Here’s what went down, and the best AI tools, tips, and prompts you’ll want to steal.
1. Smarter Targeting and Prospect Research
We kicked off with a game-changer: using AI to make sure you’re calling the right people. David Kreiger, SalesRoads, shared how his team uses Clay to qualify leads before reps ever pick up the phone. It pulls company data and uses AI to tell you if a prospect actually fits your ICP, saves hours of manual research, and gets your team focused on the right accounts.
John Buckley (from Sell Better’s Daily Sales Show) showed us Agent.ai, a no-code agent that scores a company for outbound fit with a single URL. He’s trained it on his ICP so it gives a quick thumbs-up or “hard pass.” No prompt writing needed.
Jax Gill (from Inspira Financial) took it even further. She trains ChatGPT to review a company’s website and her prospect’s LinkedIn profile, then find common ground to help her build rapport fast. She even gives it a list of her solutions and asks for possible pain points to reference in the convo. It’s like AI-powered pre-call prep, minus the rabbit holes.
Prompt ideas to steal:
- “Here’s my ICP. Here’s this company’s website. Is this a fit or not? Why?”
- “Compare my LinkedIn profile to [prospect’s name]’s. What do we have in common?”
- “Given this company and our services, what pain points can I lead with?”
2. Better AI Sales Prospecting Emails and Messaging
Let’s talk outbound emails. Doug Gibb’s team at Waste Management uses Conquer with GenAI email, which drafts emails based on past conversations and makes sure they don’t miss a promised follow-up. It pulls call and email history straight into Salesforce, so everything’s in one place.
David dropped this gem: if you write more than three emails a week, build a custom GPT. He’s trained his to match his tone and voice. Upload 50 of your best emails, and now your GPT can write in your style. It’s faster, but more importantly, it’s better.
WATCH: How to Build a Custom ChatGPT (shared by David)
James added Oliv to the mix. This tool sends him a cheat sheet before every call with company background, team bios, and even icebreakers. “Ask Chloe about her transition from radio hosting to content marketing” is way better than “Hope you’re well.”
One big reminder from everyone: AI-generated emails shouldn’t sound AI-generated. If your message is filled with fluff, jargon, or emojis in every line, it’s going straight to trash. Your prospects can smell it. Use AI to help, but still bring your brain.
Prompt ideas to steal:
- “Use my tone. Write a prospecting email for this company using the info from our last call.”
- “Summarize this LinkedIn profile in one sentence I can use as a cold email opener.”
- “Rewrite this message to sound more human, less like it came from a bot.”
3. Coaching, Confidence, and Call Reviews
AI isn’t just helping reps do the work. It’s helping them get better at it. David recommends using AI to coach yourself after calls. His reps drop their call transcripts into ChatGPT and ask for feedback. What could I have done better? What questions did I miss? It gives them a score and action steps to improve.
Jax uses AI before the call. She practices objections with ChatGPT in persona-mode. “Be a tough IT Director. Push back on cost.” It gives her reps a safe space to screw up and get better.
Doug’s team uses Conquer to transcribe and summarize every call. It flags sentiment dips, highlights next steps, and scores reps on their delivery. That all feeds into Ambition, where managers get a full coaching report before every one-on-one. And yes, even new managers can coach like pros because the system shows them exactly what to focus on.
We also shouted out Grw AI, a tool for roleplay call coaching. Reps can practice calls and get feedback based on real frameworks. It’s like flight simulator training for sellers.
I also shared how much I love using Fathom for call notes. I just click a button and boom, it gives me a clean sales summary with top pain points, current situation, and next steps. It’s fast, easy, and way more useful than generic transcripts. Use it for internal calls too to help you take notes and create to-dos.
Prompt ideas to steal:
- “You’re a skeptical IT Director. Let’s roleplay a cold call. Push back on price and security.”
- “Here’s my call transcript. What could I have done better? Give me a grade.”
- “Give me 3 coaching questions to reflect on after this call.”
4. Real-Time Insights and In-the-Moment Support
Sales moves fast. Reps don’t have time to dig through notes or scroll LinkedIn for the latest news. That’s where real-time insights come in.
James’s tip: Use LinkedIn Sales Navigator alerts. Ring the bell on your top prospects and accounts. You’ll get notified when they change jobs, get promoted, or post. Instant reason to reach out. That’s prospecting fuel your team is probably ignoring.
Doug’s team uses Ambition’s pre-read feature to prep for coaching. It pulls 90 days of call scores, KPIs, pipeline data, and even sentiment analysis so managers walk into meetings ready. Their AI-based pipeline insights show if deals are stuck, what changed, and where to focus.
David shared Trellus, a power dialer that lets reps pause mid-call to get AI-powered coaching suggestions. It’s like having a manager in your ear without the pressure.
Prompt ideas to steal:
- “Give me coaching advice based on this sales call recording.”
- “Summarize this opportunity pipeline for my one-on-one. What’s stuck and why?”
- “If my rep is below target on discovery, what should I review with them this week?”
5. AI for Inbound, Enablement, and Emotional Intelligence
You didn’t think AI was just for outbound, did you? David’s team is using Sela for inbound calls, and it’s outperforming human reps in tier-one qualification. The AI calls the lead, asks 2–3 qualifying questions, and routes the hot ones straight to an SDR. It’s efficient, repeatable, and for simple calls, often better than a live person.
James brought up Sybill, which reads facial expressions and body language during video calls. It sends post-call insights like, “Your buyer leaned back and widened their eyes when you said pricing.” That’s gold for follow-up and helps reps refine their messaging and emotional timing.
And of course, Doug’s team uses Microsoft Copilot, a company-approved, closed AI system integrated into their workflows. Their AI governance committee ensures compliance, which matters when your team is 50,000 strong.
Bonus tip from Jax: Use ChatGPT as your personal hype woman. “Give me a pre-call pep talk.” Or ask it to roast you. Either way, you’re showing up more confident.
Prompt ideas to steal:
- “Pretend you’re my mentor. Give me a 30-second pep talk before this big sales call.”
- “Roast me. What could I do better in my outbound pitch?”
- “Act like a buyer. Ask me 3 tough qualifying questions based on this service.”
READ: Confessions from a Late-Adopter: The Truth About AI for Revenue and Enablement Leaders
This session wasn’t fluff. These are real leaders, using real tools, getting real results. If your team is still scared of AI or waiting for some “perfect system,” you’re already behind.
The final takeaway?
“Use the time AI saves you to do the task better. Not faster. Better.”
– David Kreiger
TL;DR – Here are the best AI sales tools and how our panelists are using them:
- Agent.ai – James built an agent that scores companies instantly based on ICP fit, eliminating the need for prompt engineering
- Ambition – Doug uses it to prep managers for coaching with pre-read insights that include sentiment, pipeline data, and call scores
- ChatGPT – Jax shared how her team uses ChatGPT to simulate prospect objections and refine messaging before high-stakes calls; it’s like having a role-play coach on standby
- Clay – David uses Clay to pre-qualify leads and filter out non-ICP accounts, saving reps hours of manual research
- Conquer – Doug’s team uses it to auto-draft follow-ups based on call history and transcribe every conversation for coaching
- Fathom – We use Fathom here at Factor 8 to summarize sales calls and uncover real buyer pain points. Tip: Use it for both internal and external meetings to quickly extract key details, create to-do lists, and skip manual note-taking
- Grw AI – Lauren and Jax called it a flight simulator for sales; perfect for reps to practice and build confidence before high-stakes calls
- Microsoft Copilot – James noted that Copilot helps his team save time by summarizing long email threads and prepping for meetings straight from Outlook and Teams
- Oliv – James loves Oliv for the call prep emails, especially the personalized icebreakers like asking about career transitions
- Sybill – Doug mentioned using Sybill to flag buyer reactions mid-call, helping reps spot hesitation or interest and follow up more strategically
- Sela – David says Sela outperforms humans for tier-1 inbound lead qualification and is being used successfully in production
- Trellus – David mentioned reps can pause a call and get live coaching advice based on the persona or objection they’re handling
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Factor 8 Named a Selling Power 2025 Top Sales Training Company
Factor 8 is pleased to announce it has been included on Selling Power’s Top Sales Training Companies 2025 list.
“It’s an incredible honor to be named a Top Sales Training Company by Selling Power again,” said Lauren Bailey, Founder and CEO of Factor 8. “Our mission has always been to make sales a career people love, and stay in. We’re proud to keep leading the way in virtual sales training.”
According to Selling Power publisher and founder Gerhard Gschwandtner, quality sales training remains paramount to B2B sales success. “As the economy enters a period of stock market ping pong and tariff turmoil, along with the continued AI disruption within the B2B sales landscape, having an effective and forward focused sales organization is critical to maintain revenue growth. Partnering with the best sales training companies will help ensure your team’s success.”
All companies on the list submitted a comprehensive application that included a detailed listing of their offerings for both training and retention, innovative solutions, and their company’s unique contributions to the sales training marketplace.
The main criteria used when comparing applicants and selecting the companies to include on this year’s list were:
- Depth and breadth of training offered
- Innovative offerings (specific training courses, methodology, or delivery methods)
- Contributions to the sales training market
- AI impacts and integrations
- Strength of client satisfaction and overall client feedback
To evaluate applicants for the list, the Selling Power team surveyed and considered feedback from nearly 350 clients of the applicants. Here is a brief selection of comments from their clients:
- “Extremely effective. They accelerated our sales results by 10x!”
- “Having been through a couple other professional sales training programs in the past, I can state that our current choice is by far the best. Our outside sales team left the training feeling energized, enlightened and empowered. Early wins from the team are promising. The communication throughout the process was terrific.”
- “They are delivering an exceptional sales training experience. Their professionalism, knowledgeable facilitators, and well-structured courses provide valuable insights that are both practical and impactful. The training is engaging, actionable, and tailored to real-world sales challenges, making it a worthwhile investment for any sales team.”
- “As always, exceptional facilitators/consultants who understand our needs and our business and always deliver.”
- “They truly act as partners in helping to figure out what’s needed in your organization. No cookie cutter approach to training here! They really got everyone involved in discussions and engaged all of our reps. Many of our more seasoned reps started out as skeptics and ended up finding value from the training, especially relating to demos and empathetic listening.”
- “Our facilitator was fantastic and well prepared. He connected with our sales team immediately and quickly earned their trust and respect (not easy to do). The content was both relevant and digestible. The program has already improved our team’s performance.”
Selling Power magazine editors say CROs, sales VPs, and sales enablement leaders can leverage this list to find the right sales training partner to help salespeople succeed during social distancing and remote working. See the Selling Power Top Sales Training Companies 2025 list.
About Selling Power
In addition to Selling Power, the leading digital magazine for sales managers and sales VPs since 1981, Personal Selling Power, Inc., produces the Sales Management Digest and Daily Boost of Positivity online newsletters, as well as the leading AI sales newsletter (Subscribe to the AI 4 Sales™ / Sales 3.0 Digest – Sales 3.0 Conference / Blog (sales30conf.com). Selling Power is a regular media sponsor of the Sales 3.0 Conference, which is attended by a total of more than 4,500 sales leaders each year.
Looking to partner with a top sales training company?
Contact us today to learn more about our sales training programs
for sales reps and sales managers.
How Real People are Winning the Sales Prospecting Game Using AI [Webinar]
How Real People are Winning the Sales Prospecting Game Using AI
[Video Recording]
Meet the Speakers
Lauren Bailey
Founder
Factor 8 & #GirlsClub
Lauren Bailey, known to many as “LB”, is a sales leader, enablement leader, and entrepreneur and founder of 3 successful brands: Factor 8, providing front-line job training for inside sellers and managers, The Sales Bar, a subscription-based virtual sales training platform, and #GirlsClub, a community and development program helping more women earn leadership positions in sales.
My mission is to walk alongside sales professionals as they develop the skills and best practices needed to find sales success. Our purpose is to show salespeople their true worth as the tip of the spear. I have the pleasure of hosting the best minds in sales every day and creating content that elevates the sales profession.
Connect with me @saywhatsales on Instagram, TikTok, and Twitter. Join us live daily to learn and grow into a top-performing sales professional.
Jax Gill
Training Manager
Inspira Financial
Jacqueline Gill is a Senior Manager in Sales Enablement who’s been at TTEC for 12 years—which in BPO years is basically a lifetime. While her official job is enabling sales, she’s also been known to jump into learning services sales conversations once the executive sellers work their magic. Think of her as the closer with a curriculum. Outside of work, she’s a proud mom of four and a firm believer that AI can help with just about anything—except maybe laundry.
Doug Gibbs
Sr. Inside Sales Manager, Tools & Technology
Waste Management
Forty-seven years’ experience managing teams and processes across two primary industries, Retail Department stores and Environmental Solutions/Logistics. The last eleven years have been invested with the Inside Sales Teams at WM, including managing retention and acquisition teams, then progressing to exploring, sourcing, procuring and implementing 3rd party tools and solutions to significantly improve both our customer’s and Sales Team’s experiences.
David Kreiger
President
Sales Roads
David Kreiger is the founder of SalesRoads, a leading sales outsourcing firm with over 17 years of experience helping businesses drive revenue growth by building winning sales teams. A seasoned entrepreneur and host of the “Sell Like A Leader” podcast, David champions a philosophy that sales success hinges on talent development and a people-first mindset.
Building a Top-Performing Sales Team [Webinar Recording]
Building a Top-Performing Sales Team
[Video Recording]
Meet the Speakers
Lauren Bailey
Founder
Factor 8 & #GirlsClub
Lauren Bailey, known to many as “LB”, is a sales leader, enablement leader, and entrepreneur and founder of 3 successful brands: Factor 8, providing front-line job training for inside sellers and managers, The Sales Bar, a subscription-based virtual sales training platform, and #GirlsClub, a community and development program helping more women earn leadership positions in sales.
Her mission is to change lives by supercharging people’s careers and helping them love coming to work. When we feel confident and successful at work, everything is better, right? Known on the speaker circuit for her “No B.S.” style and spunk, look for LB to make you laugh, keep things moving quickly, and help you take immediate action with her tactical tips and insights.
Devyn Blume
Sr. Account Executive
Allego
Devyn is a Sr. Account Executive at Allego with 8 years of experience in sales, specializing in consultative selling and client relationship management. Throughout her career she has excelled in driving revenue growth, building strong customer partnerships, and leveraging sales technologies to streamline processes.
At Allego, Devyn focuses on delivering innovative sales enablement solutions, helping teams optimize training, onboarding, and content sharing. With expertise spanning multiple industries, she is a trusted advisor to clients seeking to enhance sales performance through technology-driven solutions.
Join Another Webinar
View our live Sales Shot webinar schedule and register for upcoming events below.
How To Build A Sales Manager Cadence (And Save Your Own Life) [Webinar Recording]
How To Build A Sales Manager Cadence (And Save Your Own Life)
[Video Recording]
5 Tips to Maximize Your Sales Training Investment
After you’ve hired a sales training vendor, there are a series of questions you need to answer in order to ensure you’re getting the most out of your sales training investment, like:
- How do I maximize sales training ROI?
- How do I measure training success?
- How do I get results FAST?
Having been both the vendor and the buyer in this equation, I definitely have some insight to share. I’ve made mistakes as the Training Director hiring a sales/sales leadership training vendor, and I’ve had clients do some really smart (and less than smart) things.
Although I could write about this topic forever, I’ve narrowed it down to my top 5 tips to maximize your sales training investment.
1. Customize the Customization. Then customize that. Twenty years ago, I paid a vendor $15,000 extra to customize the training for my company. I spent countless hours sending them examples, marketing data, and websites. I forwarded redacted emails and unpublished case studies. I just KNEW they would get the “real feel” for how special our snowflake was. The result?
The vendor added one half-page sheet to the back of the workbook with two custom role plays. TWO! The pages weren’t even numbered with the rest of the workbook. Total afterthought! Literally, nothing else was custom.
Ready for the vendor flipside? Six years ago we up-leveled all our workbooks for Factor 8. This meant I couldn’t build custom workbooks from scratch anymore for clients (the downside of totally custom is a less professional look – even a few errors). Now each of our course workbooks of about 10 pages has around 15 sections in bold red font that our Advisors tailor prior to delivery. It might be the customer’s language, an industry example, a customer voice example, specific sales objections, etc. During the live interactions, our coaches play their sales calls, coach actual delivery, and will give custom samples/scripts of every skill. That’s customization!
Tip: Get an actual list of what is tailored to your organization, its format, and when/how it is delivered.
2. Require Manager Involvement. Note: I didn’t say attendance. You need attendance AND involvement! Back when I was delivering training in an enablement organization, we were afraid to invite all the sales managers to our training. They were so busy and important (and let’s be honest, a little rude). As I gained more confidence, I would meet with them 1:1 after the training with tips on what we trained and what to look for. As I got busier, I would schedule a 15-minute meeting so I could do this all at once. When I was put in charge, I required them to come AND met with them for 30 minutes afterward.
Guess what? They still couldn’t coach the skills. Sure, they attended the training, but they didn’t participate. They didn’t come and play to win as if they, too, would be graded on their adaption of the skills. They half-listened, did some email, smiled and nodded, and stole the stage as often as possible to give sage advice.
Vendor Flipside: At Factor 8, we meet with managers before the training, require attendance at the training, train the managers on how to coach the skills after the training, give managers 3+ tools to make it easy to support and coach the training, then do a follow-up meeting with the managers on how skills went, AND certify the managers to certify the reps on the skills. It may seem like overkill, but trust me, it works.
Your ROI will be cut in half if your managers aren’t underlying the importance of using the new skills and coaching their execution. Go overboard making sure they are trained, incentivized, and supported by your vendor to do this!
3. Measure Your Heart Out! If you aren’t crystal clear on the results, KPIs, and metrics that should be impacted by the training, then you’re not ready to outsource sales training. (Really, a vendor just said that!) In fact, ask the vendor what numbers they expect to move with this engagement (and don’t hire them if they don’t know!) At some point, you’ll have to show your sales training ROI, so define during the interview stage what success looks like and then go get a 3-6 month baseline on these metrics. As a training manager, I was nervous early in my career to do this. It only took one sales leader saying, “You are not solely responsible for the 35% uptick in XYZ…!” for me to start backing down and measuring success anecdotally or with smile sheets. As I grew in my career, all I did was add two words: “contribute to.” If we measure pre and post, we can all SHARE the credit!
Vendor Flipside: I love a case study. Number one reason I don’t have one on every client? They don’t provide us with their reporting. The leader pulls the trigger on the contract and then sales managers or the enablement team are left to execute and the ask never bubbles to the top. In fact, I’d love to take contracts based on the up-side (we get paid when you improve) and have offered it many times in the past, but the baseline metrics and results weren’t available from the client.
4. Get Leadership Involved (more than they are). How do I know they aren’t very involved? I’ve had about 3 clients out of 300 who were. As a training leader, I had about none. Why is this critical? Because your attendees determine how important the training is based on what the leader says, does, and spends money on. Even if you have to write the script for the VP to kick off the meeting and send over the questions they need to ask in their 1:1 meeting afterward, take the time and do it. Otherwise, you may be the flavor of the month.
Vendor Flipside: They’re my favorite three clients ever. And when they ask for anything extra, they get it. I’ve helped them get jobs 10 years later, spoken free at their conferences, and featured them on our blogs. When a leader lends their time, voice, and stature to training, it will literally change the organization’s culture. Help convince them they’ll get more ROI by being involved. Make it easier on them with cheat sheets and reminders. These clients get double their money’s worth.
5. Focus on Long Term. Ever met with an internal client who wants you to train 5 things in 20 minutes? Me too. Try every single sales leader ever. Here’s why: Most people don’t know the difference between telling and training. That’s why their people don’t change their behavior after being told. Folks, if you want people to change what they’re doing, the training will take 5x longer than you want it to AND the support “tail” for the training will be months, maybe even years. Don’t make training an event – studies show they’ll remember about 30% of what is taught. The best leaders get this fact:
Training isn’t something you did, it’s something you do.
Vendor Flipside: Events are fun. They’re low risk and high reward. We often would have better selling days during training than normal days (live calling during training). Lots of energy, buzz, and results. But if that’s all your vendor is doing, reconsider. What about keeping skills alive? Pulling the buzz forward? Seeing skills move from the classroom to the sales floor? 15 years ago we offered a 1-day post-training follow-up. Then 90 days virtual. Now we do one-year contracts. It’s the right thing to do and the right way to do it. Doesn’t fit the SKO? Hire a speaker instead.
If you’re evaluating sales training, we’re here to help. Fill out the form or email info@factor8.com and let us know how we can help.
Want more information on how to maximize your sales training investment?
Contact us today to request information on our customizable virtual sales training programs
available for reps (and managers).