Sales teams don’t have a motivation problem, they have a growth problem.
Based on our Factor 8 Current State of Sales survey, 75% of sales reps say they want a long-term career in sales, yet only 55% believe their current company will help them grow. Sales managers echo the challenge, citing limited training and development as the #1 reason they’d leave their role, while also battling burnout from administrative work and endless meetings that pull them away from what matters most: coaching their people.
In this webinar, Lauren Bailey, Founder of Factor 8, and Erik Fowler, Chief Revenue & Operating Officer at Allego, break down the biggest skill gaps, coaching challenges, and development breakdowns holding sales organizations back and explore how AI-powered coaching is changing the game.
Learn how leading teams are using AI to:
Reduce manager workload
Personalize development at scale
Create clearer career paths that keep top talent engaged and growing
Mitigating these challenges will be a key priority for sales leaders.
Watch the video replay!
THE CURRENT AND FUTURE STATE OF SALES
Sales teams don’t have a motivation problem, they have a growth problem.
Based on our Factor 8 Current State of Sales survey, 75% of sales reps say they want a long-term career in sales, yet only 55% believe their current company will help them grow. Sales managers echo the challenge, citing limited training and development as the #1 reason they’d leave their role, while also battling burnout from administrative work and endless meetings that pull them away from what matters most: coaching their people.
In this webinar, Lauren Bailey, Founder of Factor 8, and Erik Fowler, Chief Revenue & Operating Officer at Allego, break down the biggest skill gaps, coaching challenges, and development breakdowns holding sales organizations back and explore how AI-powered coaching is changing the game.
Learn how leading teams are using AI to:
Reduce manager workload
Personalize development at scale
Create clearer career paths that keep top talent engaged and growing
Mitigating these challenges will be a key priority for sales leaders.
Sales is changing fast. AI is accelerating everything, buyers are harder to impress, and mediocre selling is getting exposed.
That’s the bad news.
The good news is also simple: the teams that win are going to be the ones who get clear, get current, and double down on human skills that actually move deals forward.
Here are the trends I’m seeing, and the practical moves to make right now if you want a strong year.
1. Get crystal clear on your goal (because nobody is coming to save you)
We’re living in the noisiest time in history. Tools. Tactics. Hot takes. EVERYONE SHOUTING (😉).
If you wait for clarity, you’ll be waiting forever.
Set your own clarity:
What is the actual outcome you want this year?
What do you want to be known for?
What do you want your next role to be?
What’s the one skill you’re unwilling to be mediocre at?
Then act like you mean it. Put it on your calendar. Build your plan around it. Stop drifting.
2. AI is not replacing you, but it is replacing “entry-level effort”
AI will absolutely wipe out a lot of low-level tasks. Anything that looks like copying, pasting, summarizing, basic research, first drafts, list building, and “good enough” outreach is getting automated fast.
So here’s the play:
Use AI to get efficient
Use humans to get effective
If you’re a rep, AI can help you research, organize, and prep. If you’re a frontline manager, AI can help you spot trends, clean up pipeline signals, and prep for better coaching conversations. If you’re a sales or revenue leader, AI can help you scale what’s working, identify risk earlier, and make better growth decisions without losing visibility into the human side of performance. If you’re in enablement, AI can help you reinforce consistency in skills and training, but it should not define what “good” looks like.
6. Demos are changing: shorter, tighter, more customized
The era of the 45-minute “power demo” is fading.
Teams are moving toward:
Micro-demos
Self-serve exploration
“Show me exactly what I asked for” experiences
Recordings that help buyers sell internally
If your demo is still a feature parade, you’re doing product theater, not selling.
Make demos:
Smaller
More specific
Tied to their use case and decision criteria
7. Call bridging is one of the fastest ways to prevent ghosting
Ghosting isn’t new. Buyers disappearing mid-deal is basically a sport now.
One of the simplest skills that helps is call bridging: setting up the next step while you still have them, with clarity and agreement, so follow-up isn’t chasing.
Quick example language:
“Before we hang up, what needs to be true for you to feel good about moving forward?”
“If we’re aligned, what’s the next best step on your side and mine?”
“Let’s lock the next conversation now so we don’t lose momentum.”
Factor 8 surveyed thousands of sales reps, frontline managers, and senior leaders to find out. Every level pointed to the same problem: prospecting. Reps call it the hardest part of the job, managers call it the biggest barrier to hitting goal, and leaders rank outbound effectiveness as a top priority. Meanwhile, the coaching that would close the gap keeps losing to meetings and admin work.
SALES REPS
60%
say prospecting is the part of the sales cycle they struggle with most.
SALES MANAGERS
63%
say prospecting-related issues are their team’s biggest barrier to hitting goal.
SALES MANAGERS
62%
are experiencing burnout at work.
SALES REPS
29%
say their manager actually makes them better at their job.
Who We Surveyed
Thousands of sales professionals across every level of the sales organization, every major sales function, and companies of every size.
Respondents are primarily based in the United States, with additional responses from Canada and other countries.
What’s the hardest part of sales for reps?
Prospecting, and it isn’t close. 60% of reps say it’s the part of the sales cycle they struggle with most, well ahead of closing, qualifying, demos, and discovery.
The struggle travels up the org chart. 63% of managers say prospecting-related issues are what’s keeping their team from hitting goal, with weak messaging, low outbound dials, and low connect rates near the top of the list.
Where reps struggle most
1. Prospecting
60%
2. Closing
3. Qualifying
4. Demos
5. Discovery
Which outreach channel books the most meetings?
Phone. Reps put 40% of their prospecting outreach into email and 34% into phone. When asked which channel books the most meetings or closes the most deals, 53% say phone. Email trails at 31%.
Where reps spend outreach time
Email
40%
Phone
34%
Social
17%
Text
9%
Which channel wins meetings and deals
Phone
53%
Email
31%
Social
11%
Text
5%
Phone gets 34% of the effort and drives more than half of meetings and closed deals.
Leaders noticed, too: 40% want their reps to pick up the phone more often.
What do sales reps want from their job and their manager?
65%
rate their manager positively
29%
say their manager makes them better
Reps like their managers. Far fewer say their manager is actually helping them improve.
85%
prefer virtual selling to reach more customers, faster. Efficiency and reach are the top two benefits reps named.
74%
want fewer internal meetings and emails so they can focus on selling. Internal meetings top the list.
52%
want more training and development in their day-to-day work, well ahead of tools and tech (35%).
43%
would leave their role without training or a clear growth path. It’s the #1 reason reps would walk, ahead of burnout.
32%
want more call coaching, skill coaching, or sales training from their manager.
Fewer 1:1s, please
Reps want fewer manager 1:1 meetings, unless those meetings include call or skill coaching.
Bonus finding: 7% of reps rated their manager a “screen door submarine.” We’ll let that one sit.
What’s getting in the way of sales managers?
Managers know what their teams need. They don’t have the hours to give it. 62% are experiencing burnout, and their biggest daily frustrations are too many meetings and admin overload.
62%
of sales managers are currently experiencing burnout at work.
23%
say CRM updates drain the most energy from their day, followed by internal meetings (18%) and forecasting and reporting (17%).
53%
say more coaching time (27%) and better rep training (26%) are what their team needs most to succeed.
What managers know they need to do
Coach consistently
Develop their team
Drive execution
What gets in their way
Too many meetings
Admin and CRM work
Rep fire drills
What are sales leaders prioritizing?
Leaders see the same gaps from the top: inconsistent execution, no consistent sales process, and coaching that isn’t happening often enough.
41%
say improving outbound prospecting effectiveness is a top priority.
#1
Coaching more often and more effectively is leaders’ top improvement priority for managers. 52% want managers to coach reps consistently.
Top 3 barriers to goal
Inconsistent team execution, no consistent sales process, and hiring and retaining sales talent.
Top skills leaders say reps need to improve
1. Time management and prioritization
2. Identifying customer challenges and opportunities
3. Building and presenting value
Top skills leaders say managers need to improve
1. Making the shift from rep to manager
2. Consistent coaching and developing reps
3. Driving process, accountability, and execution
Leaders want managers to drive the process. Managers say there isn’t one.
Listening and connecting with customers tops the list of what leaders want reps doing more of.
One problem. Three views of it.
The shared pain
Prospecting
Reps struggle with it, managers miss goal because of it, and leaders are prioritizing it.
The shared fix
Coaching and training
Reps want more development, managers want more coaching time, and leaders want managers coaching consistently.
The shared blocker
Time
Meetings, admin, and CRM work crowd out selling for reps and coaching for managers.
Want the full research?
Get every chart, breakdown, and respondent detail in the complete Sales Team Challenges and Skill Gaps infographic.
Want the full research?
Get every chart, breakdown, and respondent detail in the complete Sales Team Challenges and Skill Gaps infographic.
Citing this research?
Please do. Attribute findings to Factor 8’s Sales Team Challenges and Skill Gaps research and link back to this page.
Example: According to Factor 8’s Sales Team Challenges and Skill Gaps research, 53% of sales reps say phone books the most meetings or closes the most deals.
Top Sales Trends, Challenges & AI Tools You Need to Know
[Video Recording]
Sales Trends That Are Shaping How Teams Sell Today
We asked salespeople (sales reps, managers, leaders, and enablement pros) around the globe what’s really happening inside sales orgs. What’s driving performance, what’s draining it, and how AI, coaching habits, team culture, and skill development are shaping the way we sell heading.
This session reveals the top takeaways from our newest research, The Current State of Sales: Trends, Challenges & the Role of AI. Whether you’re a rep, frontline manager, enablement pro, or sales leader, you’ll leave with real data, fresh insights, and ideas to help your team stay competitive next year.
Here’s what we’ll cover:
The top sales trends that will shape the future
Where reps, managers, and leaders are struggling the most
The AI tools sales teams actually use, and what they use them for
How sales managers are spending their time and where they need support
What reps say they want more of to stay, grow, and hit quota
The skills and knowledge gaps slowing down sales teams
What sales leaders are prioritizing in their budgets and strategy plans
No fluff. Just practical takeaways, honest commentary, and a few laughs.
Watch the video replay!
Sales Trends That Are Shaping How Teams Sell Today
We asked salespeople (sales reps, managers, leaders, and enablement pros) around the globe what’s really happening inside sales orgs. What’s driving performance, what’s draining it, and how AI, coaching habits, team culture, and skill development are shaping the way we sell heading.
This session reveals the top takeaways from our newest research, The Current State of Sales: Trends, Challenges & the Role of AI. Whether you’re a rep, frontline manager, enablement pro, or sales leader, you’ll leave with real data, fresh insights, and ideas to help your team stay competitive next year.
Here’s what we’ll cover:
The top sales trends that will shape the future
Where reps, managers, and leaders are struggling the most
The AI tools sales teams actually use, and what they use them for
How sales managers are spending their time and where they need support
What reps say they want more of to stay, grow, and hit quota
The skills and knowledge gaps slowing down sales teams
What sales leaders are prioritizing in their budgets and strategy plans
No fluff. Just practical takeaways, honest commentary, and a few laughs.
Reps are proud, leaders are optimistic, and managers are burning out. Factor 8 surveyed thousands of sales reps, frontline managers, and senior leaders about how they work, how they feel about the job, and what would make them stay or go.
SALES REPS
75%
are proud to be in sales.
SALES LEADERS
56%
say sales feels stronger than last year.
SALES MANAGERS
62%
are currently experiencing burn out.
SALES REPS
71%
are happier working from home.
Who We Surveyed
Thousands of sales professionals across every level of the sales organization, every major sales function, and companies of every size.
Respondents are primarily based in the United States, with additional responses from Canada and other countries.
Where do sales teams work today?
Mostly hybrid. 43% of sales professionals work hybrid, 37% work from home, and 20% work in the office.
Leaders aren’t pushing for a full return. Only 10% prefer their teams in the office 100% of the time.
Where sales teams work
All respondents
37%
43%
20%
Sales reps
56%
26%
18%
Sales managers
15%
60%
25%
Leaders’ preference
35%
55%
10%
Home
Hybrid
Office
Are sales reps more productive working from home?
Reps say yes. 71% say they’re happier at home, and 60% say home is where they feel most accomplished and sell more.
Which makes reps happier
Home
71%
Hybrid
18%
Office
11%
Where reps feel most accomplished and sell more
Home
60%
Hybrid
24%
Office
16%
Reps say they’re happiest, most productive, and sell more at home.
Hybrid and office-based reps work longer hours: 7+ a day, compared with 5 to 6 for remote reps.
Do sales reps want to stay in sales?
Yes, just not always at their current company. 75% want to build a career in sales, and 75% are proud to tell people they’re in sales. Only 55% want to grow where they are now.
75%
want to build a career in sales
55%
want to grow at their current company
Reps are committed to sales. They’re less committed to where they work now.
40%
aren’t sure they want to grow at their current company. Another 5% say no way.
50%
of remote reps work 6 hours or fewer a day.
56%
primarily work from home, the most of any level.
More efficient
Efficiency is the #1 benefit reps see in virtual selling, followed by reaching more customers.
49%
actively work 7 to 8 hours a day. 40% work 5 to 6 hours.
81%
say their company provides fair opportunities for people from diverse backgrounds.
Why are sales managers burning out?
Admin work and meetings. 62% of managers are experiencing burnout, and their biggest energy drains are CRM updates, internal meetings, and forecasting. Limited training and growth is the #1 reason they’d leave.
What drains the most energy from managers’ days
CRM updates
21%
Internal meetings
16%
Forecasting
15%
Coaching prep
12%
Admin and HR tasks
12%
Fire drills and rep issues
12%
Reporting and reviews
5%
What would make managers leave their role
No training or career growth
34%
Low pay
27%
Burnout
13%
Poor leadership
10%
Toxic culture
6%
62%
of sales managers are experiencing burnout.
78%
plan to stay and grow at their current company.
90%
of managers who see themselves in leadership long-term plan to stay and grow at their current employer.
61%
want to stay in sales leadership long-term. 39% aren’t sure.
People over process
More than 60% of what managers love most about the job is about people, not process.
Home helps
Managers who work from home report the least burnout.
What are sales leaders worried about?
Pipeline and prospecting. Qualified pipeline is leaders’ #1 challenge to hitting goal, and prospecting is the top skill gap on their teams, flagged by 49% of leaders.
Biggest sales team skill gaps
Prospecting
49%
Closing
41%
Objection handling
38%
Discovery
34%
Time management
28%
Negotiation
26%
Account management
21%
Leaders chose all that apply
#1 challenge to hitting goal
Qualified pipeline
31%
Skill gaps
20%
Manager bandwidth
15%
Market conditions
13%
Budget
8%
Motivation
7%
56%
say sales feels stronger than last year. Optimism increases with job level.
22%
most want to improve the percentage of reps hitting goal, followed by new hire ramp time (19%).
Manager coaching
Over half of leaders say ineffective manager coaching is slowing team success. Coaching and development tops the list of manager skill gaps.
28%
report formal DEI goals for hiring or advancement.
Nearly half of leaders lack strong confidence in their current training plans.
54% feel confident, 22% are neutral, and 24% are not confident.
Committed to sales. Not always to their company.
The good news
Pride and optimism
75% of reps are proud to be in sales, and 56% of leaders say sales feels stronger than last year.
The pressure point
Manager burnout
62% of managers are burnt out, drained by CRM updates, meetings, and forecasting.
The retention lever
Growth
Limited training and growth is the #1 reason managers would leave, and only 55% of reps want to grow at their current company.
Want the full research?
Get every chart and breakdown in the complete infographic, and see what’s holding your team back and how training can help.
Want the full research?
Get every chart and breakdown in the complete infographic, and see what’s holding your team back and how training can help.
Citing this research?
Please do. Attribute findings to Factor 8’s Current State of Sales research and link back to this page.
Example: According to Factor 8’s Current State of Sales research, 71% of sales reps say they’re happier working from home.
What’s the most overlooked factor in sales growth? Your frontline sales managers.
They influence every deal, every rep, every forecast, and yet about 60% of new managers report they never received training when they stepped into leadership.
Let’s stop looking past the obvious. Your frontline managers are the secret to scaling sales growth.
If you want more reps hitting quota, more deals converting, stronger forecasts, and less burnout across the board, it starts with your managers. Not your tech stack. Not your latest AI tool. Not another rep enablement platform (though these are important and we love them, check out our friends at Allego).
I’ve worked with thousands of sales teams and here’s the hard truth. Most companies are investing in everything except the role that has the biggest impact on team performance and revenue growth.
And when we flip that, the results are massive. We’re talking 20 to 47% increases in rep conversion rates. And we didn’t even touch the rep. Just by developing their manager.
So if you’re planning for growth, keep reading. Because managers aren’t a bottleneck. They’re your biggest growth engine.
1. Managers Bring Consistency (and That’s What Scales)
Change is part of growth. Reps switch teams. Territories shift. Comp plans evolve. But in the middle of it all, your frontline managers keep the team focused, engaged, and aligned.
That only works when they’re supported.
Too often, every manager ends up running their own playbook. Not because they want to, but because they’ve never been shown what “good” looks like. And even when you have playbooks, they don’t get translated into everyday actions and team rhythms.
Here’s where the cracks usually show up:
Hiring: Everyone’s looking for different things. Even with a profile in place, managers need support identifying what good sounds like in an interview.
Performance management: Breaking down a big quota into measurable KPIs isn’t intuitive. And very few new managers have been trained to do it.
Rep engagement: Some managers meet weekly. Some meet monthly. Some skip 1:1s entirely. Most spend time reviewing pipeline, not developing skills or coaching.
Pipeline hygiene: Definitions for deal stages vary across teams. That makes forecasts unreliable and coaching hard to scale.
Consistency is what turns momentum into real, scalable growth. And it starts at the manager level.
Give them the tools to:
Hire with confidence using a shared rubric
Set goals and track KPIs that actually drive performance
Run a standard meeting cadence that blends coaching, performance, and career conversations
Clean up pipeline processes so everyone’s speaking the same language
Even tenured managers benefit from this kind of clarity. One enterprise team we worked with had over 10 years of management experience and still walked away from this training saying, “I wish I’d had this years ago.”
2. Great Managers Build People, Not Just Pipelines
Most sales managers were promoted from rep roles. And as reps, their entire world revolved around winning. So when things get tough, what do they fall back on?
Closing the deal.
They hop on the call. They take over the demo. They second-voice the close. It’s not bad intentions, they’re just doing what worked for them. But when a manager becomes the deal hero, the team stops learning.
And that’s when reps leave.
They leave when they don’t feel developed
They leave when they’re not hitting quota
They leave when they don’t have a strong relationship with their manager
The revolving door hurts growth. Every open seat is lost pipeline. Every green rep takes months to ramp. Every exit chips away at morale.
What helps? Redefining the manager role and giving your leaders a new toolkit.
Help them shift from deal-doer to rep-developer
Give them interaction frameworks like COACHNso coaching doesn’t feel like guesswork
Recognize managers for building people, not just saving quarters
Because a manager who builds skill, confidence, and trust is someone who retains reps, not replaces them.
We all love to say coaching is the silver bullet. And it is. But only when it’s done well.
Real coaching moves the needle on performance, confidence, and retention. But too often, what we call “coaching” is just a pipeline review in disguise.
If you’ve ever listened in and heard:
The manager doing all the talking
A rep leaving with three disjointed to-dos
A session that feels more like a performance review than a development convo
Then chances are, your managers need support here.
The most common trap? The Mini-me. That’s the manager who coaches every rep to be a version of themselves. It works for the one or two reps with the same style. Everyone else gets frustrated, disengaged, or overlooked.
Good coaching is consistent, rep-centered, and rooted in skill development, not deal rescue.
That’s why we don’t treat coaching like a one-hour workshop. It’s now a six-hour, three-part course here at Factor 8. Because shifting behavior and building confidence takes time. And when it clicks, reps perform. They stay. And they grow.
If You’re Skipping Manager Development, You’re Skipping the Scale
Let’s be honest. The biggest miss isn’t the manager. It’s us.
We’ve skipped the basics. We assume managers will figure it out because we did. We prioritize tech over training. We fix people problems with process or platform investments.
But if you want more reps to hit quota, you don’t need a new tool (yet). You need stronger conversations first.
That comes from skilled, supported, confident managers.
Most reps today get a sliver of what they need in onboarding. Then they’re tossed five tools and a quota. They’re still learning the basics. And the person who owns the rest?
Their manager.
So let’s invest in them. Train them. Coach them. Give them a framework, a cadence, and a community. Make development part of the rhythm, not a one-time event.
Because your reps aren’t going to grow if your managers aren’t growing too.
Managers are the secret to scalable revenue growth. Let’s stop hoping they figure it out, and start helping them knock it out of the park.
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AI is transforming how sales and enablement leaders work, but not every tool is worth your time. The real win comes from using AI to cut through busywork, speed up planning, and empower your team to perform at their best.
Here are the AI tools, prompts, and use cases worth stealing (and what you should skip).
Practical AI Use Cases That Are Saving Leaders Time
The biggest takeaway from our panel? AI is already drastically changing the game for sales and enablement leaders, and not in a distant future way. It’s helping them cut hours of work, make better decisions, and focus on the human parts of their job that matter most.
Helen shared a genius way to scale call reviews. Instead of sifting through hundreds of recordings, she uploads batches of transcripts into ChatGPT to surface competitor mentions, objection patterns, and whether reps are locking in next steps. It’s like a virtual coach doing the analysis for you, so you can spend time actually coaching.
Prompt to steal: “Here are 20 discovery call transcripts. Create a table summarizing top objections, competitor mentions, and whether a next meeting was secured.”
Another smart move came from Rose, who built her own “clone” using Gemini. This persona enforces the company’s tone, writes in an active voice, and ensures content is clear and consistent across teams worldwide. The result is scalable sales training that actually sticks.
Prompt to steal: “You are a sales enablement expert. Write onboarding instructions in an active voice, using customer-centric language at an 8th-grade reading level.”
AI can also help sales managers think faster and coach smarter. By feeding pipeline data into ChatGPT, Casey uses it to surface coaching priorities, the same insights an experienced leader would draw out, but in minutes instead of hours (grab Casey’s free AI toolkit for 6 AI prompts sales leaders need).
Prompt to steal: “You are a frontline sales manager. Analyze this pipeline report and highlight three coaching priorities for my next one-on-one.”
Richard is taking a different angle by using AI to power better top-of-funnel strategies. He pairs Claude with Crystal Knows to understand buyer personality types, helping him craft outreach messages that feel personal, not spammy.
Prompt to steal: “Here’s my target persona and their LinkedIn profile. Write a personalized outreach message that matches their communication style.”
These aren’t hypotheticals. They’re working right now. The leaders using AI this way aren’t just saving time; they’re leading smarter.
AI isn’t here to replace coaching (or training), but our panel proved it can make coaching a whole lot more impactful. By letting AI handle the heavy lifting behind the scenes, leaders are freeing up more time to actually coach and connect with their teams.
One of the standout examples came from Helen, who built a custom Love Your Team bot to help leaders role-play tough performance conversations. Managers can pick a scenario (easy, medium, or hard), practice with the bot, and get scored on how they did. It’s a safe way to prepare for conversations most leaders dread.
Prompt to steal: “You are an underperforming rep. Role-play a tough performance conversation with me and grade my responses.”
Rose is embedding AI directly into enablement the right way: skills first, AI second. Her team uses NotebookLM to create an interactive, searchable knowledge base from training content. Reps can ask it questions, generate FAQs, and even turn the material into podcasts in multiple languages, making learning easier to access and retain.
Prompt to steal: “Based on this training content, create an FAQ for reps that focuses on what they need to do, not just what they need to know.”
GRW also came up as a powerful tool for role-play coaching, giving reps a safe environment to practice calls and get real-time feedback based on proven sales frameworks (like the Factor 8 COACHN Model).
Casey encourages leaders to train their GPT to think like them. By feeding it prompts that teach their leadership style and decision-making frameworks, managers create a digital “thinking partner” they can lean on for coaching plans and tough conversations.
Prompt to steal: “Here is how I coach and communicate with my team. Learn my style and use it to draft coaching plans for these three reps.”
AI works best when it reinforces fundamentals instead of replacing them. Richard uses it for pattern recognition in sales scenarios, helping reps see what makes deals successful before they automate a thing.
Prompt to steal: “Analyze these sales scenarios and identify patterns in what led to successful outcomes.”
The bottom line? AI makes coaching and training more scalable and personal, but it only works if you use it to strengthen (not sidestep) the human connection.
Table Stakes for Using AI Safely and Effectively
AI is only as good as the guardrails you set around it. The panel made it clear that using AI safely and effectively isn’t optional, it’s table stakes.
Privacy and data control came up first. Casey stressed that leaders must lock down privacy settings before letting teams run wild with new tools. Without clear guardrails, you risk exposing sensitive information.
Prompt writing was another critical theme. Richard shared that the best outputs come from clear inputs: provide context, be specific, and always state your desired outcome. “Bad prompts get bad results,” he said. That’s why he often uses Claude to refine his prompts before sending them to other AI tools.
Helen showed how simple prompts can turn messy CRM data into clean, actionable summaries. Instead of spending hours in spreadsheets, she asks ChatGPT to create a table showing seller progress against objectives, giving her an instant snapshot of where to focus.
Rose brought it back to basics: start with the customer, not the tool. AI is there to help you serve buyers better, not to replace thoughtful strategy. When teams lead with AI instead of empathy, they risk losing the human connection that closes deals.
The message from all four leaders? The tools will not save you unless you teach them who you are, control what they see, and use them to make your work and your relationships stronger.
One of the best parts of this session was hearing the little hacks leaders use to save time without cutting corners. These weren’t big, shiny tech demos; they were practical shortcuts anyone can use.
NotebookLM was a fan favorite for Rose, who uses it like an interactive playbook. Instead of digging through static training docs, her reps can ask it “how do I” questions and instantly get answers. It can even generate FAQs or spin training material into podcast episodes in multiple languages, making learning accessible and easy to consume.
Casey shared how she teaches leaders to train ChatGPT to think like them. By feeding it prompts that define their leadership style, tone, and decision-making process, they turn it into a virtual assistant that knows how they would respond. This saves managers countless hours on repetitive tasks like drafting coaching plans or preparing for one-on-ones.
Richard uses Claude to sharpen his prompts before sending them to other tools. He calls it a “prompt coach” because it helps him ask better questions, which leads to better outputs everywhere else.
Helen keeps her workflow lean by asking AI to summarize CRM and call data into quick performance snapshots. Instead of pulling endless reports, she gets an at-a-glance view of what’s working and what’s not so she can spend her time coaching, not crunching numbers.
Fathom was another fan-favorite for turning meeting recordings into clear, actionable summaries, so leaders and reps can skip manual note-taking and focus on next steps.
For me, Oliv is the standout AI tool for saving time. I raved about it during the webinar, sharing how it delivers all my pre-call research straight to my inbox. No digging, no scrambling, just everything I need ready to go before the call. Oliv’s AI agents handle the admin grind behind meetings, from updating CRM fields to building follow-ups and proposals. For leaders, it automates forecasting and pipeline reviews, keeping everything accurate without the manual chase.
These hacks may seem small, but together they save hours each week and keep leaders focused on what really moves the needle.
What AI Tools Are Worth It (And What to Skip)
When it comes to AI, there’s no shortage of shiny new tools, but only a handful are truly moving the needle for leaders. The panel didn’t hold back on sharing their favorites and the ones they’d leave behind.
For writing and content creation, Claude was a unanimous favorite. Both Richard and Rose rely on it for everything from drafting social content to formatting training materials. Richard even uses Claude to help craft better prompts, giving him cleaner outputs faster.
On the enablement side, Rose swears by her custom Gemini persona, the “Rose Clone,” to enforce tone and consistency in every piece of training content. She pairs it with NotebookLM to turn training materials into interactive, searchable resources that reps actually use.
For leaders coaching teams, Casey’s toolkit is full of must-haves. She loves using ChatGPT to analyze pipeline data, surface coaching priorities, and act as a sounding board for tough management decisions.
The session also spotlighted presentation tools worth bookmarking. Richard uses Napkin and Beautiful to quickly create clean, high-impact visuals, and pairs them with Canva for easy team collaboration. These tools make it faster to produce presentations that actually engage audiences without spending hours designing slides.
Not all tools got glowing reviews. Helen warned against relying on AI to write prospecting emails or LinkedIn outreach. Tools that blast generic messages do more harm than good. Her advice? Skip the automation here and pick up the phone. “Calling is back,” she reminded us. (We don’t think it ever went away 😉).
The panel also flagged a common mistake: blindly trusting AI outputs. Whether it’s using ChatGPT to summarize CRM data or leaning on any tool to draft content, accuracy isn’t guaranteed. Every AI output still needs a human eye before it goes out the door.
The takeaway? Tools like Claude, ChatGPT, Gemini, NotebookLM, and even quick-hit design tools like Napkin and Beautiful are worth the investment because they solve real problems. Tools that replace personal outreach or encourage copy-paste shortcuts? Skip them.
What’s Next for AI in Sales Enablement
The session wrapped up with a clear message: AI is here to stay, but how you use it determines whether it helps or hurts.
Helen reminded everyone not to let AI erode trust with customers or teams. Human connection still wins, and AI should support (not replace) that.
Richard sees the next wave already forming. AI agents acting like digital employees are coming fast, and they’ll change how leaders think about efficiency and staffing.
Casey urged leaders to focus on amplification. Use AI to make what you do best even better instead of trying to automate it all away.
And Rose left us with the simplest but most important reminder: no AI tool fixes bad fundamentals. Skills come first. Layer AI on top to scale and reinforce, not as a shortcut.
The future of sales and enablement isn’t human vs. machine. It’s human with machine, and leaders who embrace that balance are already pulling ahead.
When I asked the panel if AI would replace sellers, the chat blew up with a resounding “NO.” That moment sparked an important reminder from Casey about how we should approach AI:
“AI will only replace humans if we let it. Use it to make yourself better, not to take yourself out of the equation.”
The Best AI Sales & Enablement Tools
Here are the top AI tools from our panel and how they’re being used to save leaders time, improve coaching, and scale enablement:
Beautiful – Creates polished, high-impact presentations without needing a designer.
Canva – Makes it easy to design presentations and enablement content quickly with team collaboration.
ChatGPT – Analyzes call transcripts, summarizes CRM data, role-plays tough conversations, and acts as a manager’s thinking partner.
Claude – Used to draft content, refine prompts, and create cleaner outputs for training and social selling.
ConnectAndSell – Speeds up live calling efforts and list enrichment for sellers.
Crystal Knows – Helps tailor outreach messaging based on buyer personality profiles.
Fathom – Automatically summarizes calls and meetings into actionable notes.
Fireflies – Transcribes and summarizes meetings, saving time on manual note-taking.
Gamma – Builds presentation slides in minutes with AI-generated layouts and content.
Gemini – Powers custom personas like Rose’s “clone” for consistent content creation and translates training content across languages.
Gong – Analyzes call recordings to surface buyer sentiment, track deal risks, and give managers data-driven coaching insights.
GRW – Acts as a sales role-play simulator that provides real-time feedback based on proven coaching frameworks.
Kronologic– An AI-powered scheduling assistant that automatically books meetings by recognizing when a lead is ready and sending a calendar invite from the rep’s email.
Magi – Gives leaders access to multiple AI models like Claude and GPT in one interface, streamlining experimentation and prompt testing.
MidJourney – Generates high-quality visuals and creative assets for content and enablement.
Napkin – Quickly generates clean slide visuals and presentation graphics.
NotebookLM – Turns training materials into interactive playbooks, searchable FAQs, and even multilingual podcasts.
Oliv – Delivers pre-call cheat sheets with bios, company background, and personalized icebreakers to reps.
Perplexity – Acts as an AI-powered research assistant for quick, accurate information retrieval during content creation or planning.
RightBound – Uses natural language queries to create targeted prospect lists quickly, saving time on manual filtering.
Bonus: AI Tools Recommended by Attendees
Our audience came ready to share their own favorite tools. Here are a few worth exploring:
Adobe Firefly – Leveraged for generative design and creative content projects (shared by Jim).
Autobound – An AI-powered email writing tool that combines Claude and Gemini to craft smarter outbound messages (shared by Jason).
Calendly – Now includes AI-powered note-taking, recording, and meeting summaries to streamline follow-ups (shared by Viveka).
Copilot (Microsoft)– Used by several attendees to act as a virtual assistant, helping with meeting prep, drafting content, and automating repetitive tasks to boost productivity (shared by Jessica, Sandra, Angela, and Shawn).
Custom Personas for ChatGPT – A resource with 300 pre-built persona templates to customize ChatGPT for specific roles or scenarios (shared by Demont).
Otter – Helps transcribe meetings and create searchable notes; also praised for its robust subprocessors (shared by Demont).
n8n – Used for building automation workflows that connect multiple tools and processes seamlessly (shared by Jason).
ScreenApp – Captures and analyzes face-to-face meetings, providing outputs similar to Fathom for call insights (shared by Guy).
Vengreso FlyEngage – Designed to boost LinkedIn engagement through personalized messaging and workflows (shared by Viveka).
ZoomInfo – Used to create buying groups and surface intent signals to target prospects more effectively (shared by Glenn and Demont).
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Sales Manager Fears, Fails, and Fixes: Fast Actions to Prevent Burnout & Failure!
[Video Recording]
Fast Ways to Help Sales Managers Thrive
Each year we work with hundreds of front-line revenue warriors, and they tell us their secrets (😱). Come learn the 3 Fs of your sales management team:
FEARS they have you probably don’t know.
FAILS they’re making right now and how to prevent them.
FIXES they want from you but aren’t asking for.
Tiny fixes, easy questions, and small investments that will lead to better team performance quickly and PREVENT BURNOUT (LinkedIn recently reported nearly 50% of Sales managers are burnout!)
This session is JAM-PACKED with insights, low-cost/no-cost tips you can enact TODAY, and tactics for helping your sales managers survive the grind, thrive on the job, and get better results!
MUST-WATCH for all Sales Leaders – Sales Directors, Enablement Leaders, and Sales Managers!
Watch the video replay!
Fast Ways to Help Sales Managers Thrive
Each year we work with hundreds of front-line revenue warriors, and they tell us their secrets (😱). Come learn the 3 Fs of your sales management team:
FEARS they have you probably don’t know.
FAILS they’re making right now and how to prevent them.
FIXES they want from you but aren’t asking for.
Tiny fixes, easy questions, and small investments that will lead to better team performance quickly and PREVENT BURNOUT (LinkedIn recently reported nearly 50% of Sales managers are burnout!)
This session is JAM-PACKED with insights, low-cost/no-cost tips you can enact TODAY, and tactics for helping your sales managers survive the grind, thrive on the job, and get better results!
MUST-WATCH for all Sales Leaders – Sales Directors, Enablement Leaders, and Sales Managers!
