Coaching Frontline Managers To The Next Level | Sales Leader @ Webflow

I help new and first-time sales managers become great, faster.

After leading 5 SaaS sales teams across SMB to Enterprise, I’ve seen the same pattern over and over again:

👉 talented reps get promoted to management
👉 manager enablement is minimal to non existent
👉 performance stalls (or they burnout)

I believe manager enablement is one of the biggest gaps in SaaS, and it’s the fastest way to unlock predictable revenue and healthier teams.

What I believe in:

• Building cultures rooted in growth and accountability
• Knowing the numbers and forecasting with confidence
• Developing high-performing teams that break records
• Coaching people to be better, professionally AND personally
• Using health and wellness as a performance advantage

What I’ve done:

• Helped scale SaaS teams up to 10× revenue (Outreach, Webflow)
• Hired and trained 100+ AEs and 20+ managers
• Built and led onboarding & enablement programs specifically for managers
• Led teams across SMB, Mid-Market, and Enterprise

If you’re a new sales manager who wants to:
✔️ coach with confidence
✔️ run tighter forecasts
✔️ build a team people actually want to be on

Let’s connect.

Sean Gentry

I switched to Claude last week.

holy moly

This is truly what got me (after using GPT for months) 

I'm not outsourcing thinking anymore. I'm amplifying it.

Here's what I mean. Real use case - 

I dumped our entire open pipeline into Claude (SFDC CSV). Over a hundred opportunities across my segment. Raw data. No framing.

Then I asked it to find the patterns I'm missing.

Within minutes, it surfaced something I'd been blind to: my team was sending 15 emails for every 1 call.

Industry standard is 5 to 1. Yeesh. 

We weren't losing deals because of discovery. We weren't losing because of positioning. We were losing because we were typing instead of dialing.

That insight didn't come from me running reports. It came from me working with the tool to see what I couldn't see alone.

ChatGPT felt like a nice chat on a Saturday. Claude feels like partnership.

One was automating my work. The other automates my blindspots.

The crazy part is that I feel like I'm barely scratching the surface!

Helping Sales Managers Build High-Performing Teams & Predictable Revenue || Director of Sales, Docebo

I worked my butt off for this. 

To be able to come up to the mountains for thr weekend with my family. Be in the snow. Make a fire. Slow down. 

Feels damn good to be here. 

WFC complete. 

Work. From. Cabin. Tell me a better place to prep for the week… I’ll wait. 

For those of you grinding for something, keep going.

No alternative text description for this image

I've interviewed over 1,000 sales candidates.

I've gotten to the point where I no longer care about your close rate, your president's club, or your quota attainment.

I care about one thing: 

what do you do the moment after you get feedback?

I had a candidate bomb their mock discovery call in a final round interview. Not a disaster, but rough.

We gave them feedback. I pointed out what they missed.

They looked at me and said: "Can I do it again?"

I'd never heard that before. 

Not once. In a thousand interviews.

They didn't get defensive. Didn't explain why the format was unfair. Didn't wait to apply the feedback in some future job.

They wanted to apply it in the next five minutes.

That rep is one of the best hires I've ever made.

I've learned thet skills are transferable. Being coachable is rare. 


Take it from me... A former bartender.

Ok I need y’all’s opinion…

I’ve been using ChatGPT for about a year, paid and upgraded. At this point I have folders, projects, reminders, etc. I use it for work, personal, fitness, diet, finances, my Airbnbs. 

I’d say it knows me pretty well. 

There is a ton of competition in the market with Gemini, Claude, etc. 

Is it really worth going to another when I have invested so much time?

If so, I’d rather do it now than later. 

Which AI will be the best long term? Should I make the switch? Dont steer me wrong!

Ok I must know. Real talk.

Has anyone actually ever commented "Claude" on a post, received the DM and been able to 50 new GTM meetings with the info received?

Or is it all just... ****

What is even happening on this site?

If you aren't using "Projects" in GPT or Claude, you need to be. Now.

This was me. Opening up ChatGPT or Claude and starting every session by re-explaining myself.

"Here's my role. Here's my company. Here's what I'm working on. Here's how I like to communicate."

Every. Single. Time.

But one of the most underrated features nobody talks about in GPT or Claude: Projects.


Now I have separate project folders for each part of my work. 

My sales leadership role. My LinkedIn content. My Airbnb business. My workout schedule and diet. 

Each one has memory. Each one knows the context.

I open my LinkedIn content project and it already knows my voice, my audience, my content pillars. 

I open my renewals project for work and it already knows my segment, my team structure, my coaching priorities.

I'm not onboarding Claude every session anymore. I'm just working. Never starting from scratch. Its clutch.

If you're using Claude or GPT without Projects, you're doing it the hard way.

Set it up once. You'll never go back.

Setting up co-work is whole other beast. If yall want to know how to do that, I'll talk about it next.

Most AMs aren't underperforming because they lack skill.

They're underperforming because their manager never told them the job was bigger than they thought.

"Manage the account" is the wrong frame from day one. It tells people to maintain. Status quo. To not lose what's already there.

As I am building out the team here at Docebo, I am not looking to hire account managers. I want to hire account owners.

The difference is a standard.

An owner doesn't wait for the QBR to find out how the account is doing. They already know because they've been in it every week.

An owner doesn't escalate problems. They bring a recommendation and ask for input.

An owner doesn't celebrate a renewal. They see it as the floor. The expansion conversation started 90 days ago.

Here's the truth out loud:

If your AMs are "managing" that's a manager problem. Not a them problem.

The leader sets the expectation. The leader decides what good looks like.

Most managers won't do that. It's uncomfortable. It requires them to admit they've been accepting less than they should.


The ones who do it? Their teams look completely different 6 months later.

Lets go change some sh*t!

I got super sick two weeks ago. Missed 3 days of workouts. I know I know... sorry me.

By day 3 I could feel it... and it wasn't just physical.

My patience was shorter. My focus was off. I was reacting instead of thinking.

Working out isn't just about staying in shape for me. 

It's about showing up as the version of myself my team actually needs. The reps, the managers, my leaders. They get a worse version of me because my routine was disrupted.

Its taken me years but now I know that how you treat your body is how you lead. The two aren't separate.

Everyone is different so I have to ask - 

What's the non-negotiable habit that keeps you sharp when life gets in the way?

One of the best things I've done as a leader recently:

Told a rep to take the day off. No agenda. No catch-up. Just go. 

They came back the next day with more energy than I'd seen in weeks.


Here's what most managers miss: you can't coach someone who is about to burnout. 

You can push, hold accountable, run the play but if they are fried, its just for show. 

To be honest, I am always afraid of the panic quit. The "I can't do this anymore" conversation. 

Ive learned that the fastest way to lose your best rep isn't a bad comp plan. It's ignoring their energy levels.

Stop making comments if you are on the sideline.

Look, I'm sure 90% of us have read Atomic Habits. 

But one of my favorite lines in there isn't one of the more popular ones. 

James Clear says that winners and losers have more in common than the people on the sidelines.

Both put in the work. Both have bad days, bad quarters, bad years. Both deal with self-doubt, bad luck, and things outside their control.

The difference is rarely talent.

It's who keeps going when the result isn't there yet.

The commentary from the sideline these days is easy. You can see it in the comment section is you scroll way down lol

"They got lucky." "The market was different." "They had better resources."

The people actually competing know the truth: the gap between winning and losing is a lot smaller than it looks from the outside.

Get in the damn ring before you comment.

Quick show of hands... who has worked on vacation?

Or even worse, working at night while Netflix is on...

I used to do this all of the time, but it was to build call lists. 

Manually building out who to dial.

Painfully checking emails.

Praying the data was still accurate.

All so my reps could actually call the right person 


That's 5 hours I wasn't coaching.

5 hours I wasn't in deal reviews.

5 hours I wasn't at my kid's soccer practice. (thank god its only 60 minutes)

Then I found FullEnrich

Now that same work takes me 20 minutes

Here's what changed:

→ Waterfall enrichment across 15+ data sources 
 → Real-time email verification (no more bounces killing my reps' sender reputation)
 → Bulk enrichment that actually works 

My reps get better data

I get my time back

Last Tuesday, I closed my laptop at 4:30pm. Picked up my kids from school.
Made dinner. Played basketball in the playroom.

All because I wasn't stuck in spreadsheets.


Here's the thing about sales leadership:

The job will take every hour you give it.

Tools like FullEnrich just save time. 


If you're still manually enriching data, you're choosing busy work over better time.

PS - I'd rather be here than looking for people's emails...

The first time I had to give hard feedback to someone who used to be my peer, I was scared as ****

I rehearsed it close to 10 times in the car before I walked into the office.

I knew what to say. The numbers were clear. 

But saying it to someone I used to grab lunch with was a different beast.

For months I softened everything in our 1:1s. I left room for interpretation, made sure no one left a conversation feeling bad. I called it coaching. That way it was just easier for me.

This person was struggling. Missing targets. Behind on their tasks. It wasn't pretty. 

But I knew what had to be said. 

The shift came when I separated the two questions I had been treating as one: 

1. how will this land on our relationship
2. what does this person need to hear to improve

I was scared of the answer to the first if I'm being honest. 

Managers who struggle with accountability usually skip the foundation. Clear expectations, set early, before anything goes wrong. 

With that in place, a hard conversation was the start of a correction. Without it, I was doing us both a disservice. 

I learned that when you soften feedback to protect a relationship, you're choosing your own comfort over their growth. 

Bottom line was that the version of me that never gave that feedback thought he was being kind. He was just scared.

We have over 150 renewals in Q2 for current accounts. 

This week I dropped them all into Claude Cowork. And here's what it found in 10 minutes that would've taken my team a week.

I downloaded the CSV, went to cowork with my skills and prompts to identify 3 things:

1. Where are the communication gaps?
2. Which accounts are underusing the platform?
3. Where should my reps be spending time right now, regardless of ARR?

That last one matters more than people admit. And this is where we have gotten bogged down in the past. 

Most teams protect their biggest ARR and hope the rest renews. That's not a strategy. 

What came back in a matter of minutes was NUTS. It basically gave me a prioritization map we didn't have before.

Accounts we assumed were healthy had gone dark on communication for 60+ days. 

Accounts with low platform usage that nobody flagged, because the dollar amount felt "safe." 

Reps spending energy on accounts already locked in, ignoring the ones that were going to bite us in the ass with churn.

The tool didn't just surface risk. It told us where to go first. That's the shift I keep coming back to.

I'm not using AI to replace the rep's instinct. I'm trying to use it to make sure their instinct is pointed in the right direction.

I'm either working myself out of a job, or creating a new job because of it. 

Hoping it's the latter.

I really can't hate on anyone that is deciding to write their posts with AI

But I feel like there is a good and bad way to do it. 

Or should I say, a good and a lazy way to do it. 

Bad/Lazy - 

You open GPT/Claude and say "write me a LinkedIn post about making more dials/booking more meetings/hitting my goals"

You copy and paste the slop into post and hit enter. Boom, you hit your quota of one post per day. 

I know this because I've done it. Luckily only 255 people saw it. 

The Good/Better

You have an idea and record it with your voice in your voice notes. You enter the voice note into GPT/Claude to refine the thinking. You ask it to challenge your thoughts playing the devil's advocate. You go back and forth throwing new ideas into the mix to form one cohesive thought. It comes back with a post that is not only thought provoking but may challenge traditional norms. 

I've also done this and they have performed very well. It has even caused me to think differently on some topics. 

AI is getting a slop reputation. 

Note to myself: Don't get sloppy.

🔢I Coach Sales Teams to achieve consistent results by prioritizing accountability, strategic coaching, ICP focus and performance metrics | 1 on 1 and Group Coaching | LI Live and Podcast Host

When I first got into sales, I had a similar path as most. I was trying to figure out how to sell, and once I did that had my eye on being the top performer on my team, so I would be thought of as a leader and have a chance to be promoted into management.

A short year and a half later, I did all of that and was promoted. I was going to change everyone's life and get to teach the low performers how to be successful and sell. About a month and a half later, I was wondering what happened. Nobody seemed to be listening to me or at least improving like I thought they should. I was really good at chasing and closing deals because that is all I knew how to do. My boss kept telling me you are trying to be a hero "You can't save everyone."

My problem was I was subjective and emotional about everything. I had no management process. It wasn't until I figured out that I had to take the emotion out of it and make everything objective that I started to see results. 

Fast Forward 10 years later, with many successes and failures I created a 6 step process that helps takes the complication out of managing salespeople with a heavy focus on your team's Structure vs Pipeline:

1. ATM Approach- Where am I at with my team today
2. Interview Process- How do I hire more awesome Reps
3. Onboarding- How do I get new reps to revenue faster
4. Expectations- Set clear expectations so people know if they are good at their job or not
5. Coaching- How do I develop people using data
6. Ideal Customer Profile- Who are your target accounts

If interested in learning more you can visit my website to book a call or download my e-book on the ATM Approach.

mattdferguson.com

Matt Ferguson

That was awesome.

If you were rooting for the USA.
It didn’t seem like we were gonna get a shot on goal,
Let alone score.

But they hung in there long enough for the rules to change.

Sometimes that’s what you have to do.
Hang in there long enough
For something to change in your favor.

Then take advantage of it.
Even if it costs you a couple of teeth.

Congrats, USA, and great effort by Canada.
Hang in there Adam Halberstadt.

Coaching Sales Leaders to become more confident: Clarity + Accountability = Consistent Results

5 years ago, my day started as most did.

I put my daughter in the stroller, started walking, and called my brother.

I could tell you every detail about that convo.

Unfortunately, it was the last one.

Death is a weird thing.

When you lose someone.
It doesn't really get better.

You just kinda get used to it.

I always look for signs of him.
The best I know how is when I see his number.

78

I see it all the time.

On a license plate
My McDonald's number
The temperature in my car
Someone's street address on our walks

I smile and say to myself.

Hey Big Daddy

And go about my day.

If you see the number 78 today
Say hi to my brother Drew for me.

And then go call someone you love.

You never know when it will be the last time.

Small wins = Big wins

12 years ago this month, I was promoted from Top Performer to Sales Manager. Here are 12 things I know now that I wish I knew then.

1. My way wasn’t the only way.
2. You can’t make everyone you.
3. Don’t try to do everyone’s job.
4. 1-on-1’s are not a pipeline review
5. Look for the good in reps, not the bad.
6. Think before you react (Wait 20 minutes).
7. Make your people's lives easier, not harder.
8. Try to limit telling people “When I was a Rep.”
9. Make everything Objective versus Subjective.
10. People won’t follow you because you could sell.
11. Selling your team harder than selling prospects.
12. Being curious is more productive than being furious.

Sales Leaders, what would you add?

Read the quote below today.
And immediately read it 2 more times because...

I often:
Let someone's opinion bother me.
Let someone's behavior annoy me.
Let someone's mood affect me.

And have nobody to blame but myself.
All it does is slow me down.

Something I’m always working on.
Because most of the time…

The person I’m letting bother me.
Isn’t thinking about me at all.

I'm sure I'm not the only one.
So thought I would share.

An exercise every sales team should go through.
We spend way too much time dwelling on what goes wrong.

Earlier this week, I could see a team drowning.
Busy season.

A lot going on.
A lot going right…
But also a few things going wrong.

And like always, guess what gets all the attention?
The wrong.

You’ve seen it before:
Book a meeting → No show
Get a verbal yes → No signature
Finally get a yes → They cancel

So I did a simple exercise with the team.
First, we listed everything that could go wrong.

Then I asked:
“How often does it actually happen?”
One rep said,
“Every day.”

Then I asked,
“How does it make you feel?”
One rep quoted the movie The Replacements:
“Like I’m in quicksand.”

In the movie, the coach asks the players about their biggest fears.
The quarterback says quicksand.

Because once you're in it…
One problem leads to another.
And you can’t seem to get out.

I see this all the time in sales.
Something goes wrong, usually something we can’t control.

And suddenly we waste an entire day… week… or even month thinking about it.

Then we look back and ask:
“Why did we spend so much time on that?”

Like my dad always says:
It’s okay to be down.
Just don’t stay there.

We make most things bigger problems than they really are.
Talk it over with your team and get agreement on that.

Most things are just a small bump in the road.
Don't make it quicksand you can't get around or get out of.

Sales Leaders: How do you help your team reset when things start going wrong?

Ryan Holiday opened his talk on Stoicism with a simple point:
We’re dealing with the same problems people did thousands of years ago.
Then… a phone rang.

“They just didn’t have that.”
Technology has changed.
People haven’t.

Here are 3 ideas that stuck with me:
1. Discipline builds character
Easy to say. Hard to do.
I always come back to this:
Hard now → Easy later
Easy now → Hard later

2. Speak the truth, even when it’s not popular
Say what you know is right.
Not what gets likes.
Not what avoids conflict.
Short-term approval vs long-term respect.

3. Focus on what you control
Simple. Not easy.
We all drift.
But the more you control your inputs,
The better your outcomes.

All true 2,000 years ago.
Still true today.

It got me thinking about sales.

Pictured with me is Evan Romero, my first-ever client.
He’s about to make a jump I made 15 years ago:
Joining a startup with zero revenue.

A lot has changed since then.
But the fundamentals haven’t.

3 Things I will say over and over to him:

1. Know your ICP
Who do you solve real problems for?
Focus there. Ignore the rest.

2. Build your process
Figure out what works.
Then do it again and again.
Consistency over everything.

3. Know your math
Activity → Pipeline → Revenue
Know why you're doing things
So you keep doing them

We overcomplicate sales and life.

The basics aren't exciting.
But they work.

The game evolves. The fundamentals don’t.

Ryan McMichael- Loved your post this morning.
Recorded this yesterday!

Similar message
And as I commented on your post today.

Life is actually easier when you look at everything this way.

Ryans post in the comments.

When leading, it almost always comes back to the top.
Whether you’re cleaning up pee…
or trying to figure out why close rates are down.

My son told me he had to pee this morning.

So we took his pants and diaper off
and pointed him to the toilet.

By the time I realized he wasn’t tall enough…
It was too late.

He was proud of himself.
All I saw was the mess I had to clean up.

I laughed.
He had the best intentions.

I just didn’t set him up for complete success.
I see this with many sales teams

The leader has good intentions.

They put a process in place.
The reps think they’re doing a good job.

Then… they pee on the ground.
And we get frustrated with the rep.

Instead of asking ourselves:
How did this happen?

Just like I forgot the step stool.
Don’t get furious. Get curious.

Because most performance problems
are actually setup problems.

We’ve all heard it:
“Control what you can control.”
But most people never break it down.

I love how Keith Weightman does.

He simplifies it into 3 things:
1. Attitude
2. Effort
3. Skill Set

On the newest episode of The Podcast for Sales Managers, we went deeper.

Including his 5 Rules to Be Better in 2026.
Rule #1:
The 5-Hour Rule.
 1 hour a day.
 5 days a week.

Learning. Sharpening. Improving.

We also talked about:
• Why being your best doesn’t mean being “on” all the time
• Why systems > grinding harder
 Why long-term trust beats short-term wins


Links to full episode are in the comments.
Thanks for coming back on, Keith.

If you’ve ever said, “They should just know this by now…” read this.

The #1 mistake I see sales leaders make, including myself.
We assume.

We assume:
They know what to do.
They know the standard.
They know what happens if they miss it.

Most don't because we don't clarify this enough.
And nobody is a mind reader.

Easy Question to ask yourself:
At 4 pm on Friday, does your rep know if they had a good week?
If it’s fuzzy, you need to make this clear.

Role Clarity, Here is the definition:

"The degree to which employees understand their specific job duties, responsibilities, performance goals, and how their work contributes to the organization's objectives."

Clarity + Accountability = Consistent Results.

Most accountability problems are actually clarity problems.
Fix the first one. The second one gets easier.

Sales Leaders, here’s a shortcut for evaluating your reps:

A famous quote that relates to sales more than you think.

“You are the average of the 5 people that you spend the most time with.”

When you receive 3 different texts about the same thing before 5 am, you take notice.

As I read it in today's Daily Stoic message, I smiled.

My parents ingrained a similar message into me growing up.

“You are who you hang out with.”
Sometimes I listened, sometimes I didn’t.”

And over time, I have found it to be true.

Over the years in Sales, I have found the same to be true and say:

If you want to know the type of rep you have,
Go look at the best 5 opportunities they are working on.

Right targets, messaging, personas, etc...

I will add something said below:
What are they reading or listening to that is developing their skills?

If you have some people who are struggling.
Just look into these.

It will tell you all you need to know.

PS- The Daily Stoic is one page a day.
A great way to start or end your day.

The second biggest gripe I get from sales managers besides why can't they close more deals.



Why don't they close better deals?

Text below is a quick reminder.

What I almost always find is that "deals" aren't objectively defined.

Ask yourself today
Is my team working on the right deals?
Or the wrong deals?

Every second they spend on something wrong.
Takes away from something that is right.

If it isn't defined, do it today.
Everyone will thank you later when they see their paycheck.

Were you going to dedicate yourself or your team to being better this year?

And find yourself almost 2 months in and haven’t done much.

If you need a jumpstart and want some simple things to follow.

Come join Keith Weightman and me today at 10:00 PT/ 1:00 ET.

As we discuss his 5 Rules to Become a Better Seller in 2026.

Along with:
How being your best self doesn't mean having to always be on
Why systems > working harder in sales leadership
Leading with long-term trust over short-term wins

The invite is in the comments. Click attend, and we will see you there.

You weren’t set up to succeed.
Or…
You were given the opportunity to define success.

Spoke with a friend of mine who recently started a new position.

- Every piece of tech you could have.
- Been sent 27 spreadsheets
- No expectations
- No onboarding

Their marching orders
Get in there and grow the vertical.

Btw- one they have never worked in.

The BAD news:
YOU HAVE VERY LITTLE DIRECTION.

The GOOD news:
YOU HAVE VERY LITTLE DIRECTION.

Everything has perspective.
There is no direction.
Because nobody really knows.

It allows you to come up with it.

Make a plan.
Show it to your boss.
Get alignment.

Then do it and report back.

Vs the alternative.

Wander around aimlessly.
Wait for direction.
Have no clue if you're doing the right thing.

Do you want to play Offense or Defense?
Be Proactive vs Reactive.

Give me offense every time.
The choice is yours.

Side note: I do not recommend doing this to new hires!

I don’t know about you, but I can’t get enough of the “What were you like in the 90s” videos.

Maybe it’s the Goo Goo Dolls song.
Maybe it’s just realizing how fast it all went.

Because the saying is true:
Days are long.
Years are short.

And nowhere do you feel that more than in sales.
I talk to a lot of people in tough spots.

My two questions are always the same:
1. Do you believe in what you’re selling?
2. Can your boss actually help you grow?

If yes → stick with it.
If no → it might be time to move on.

Because before you know it…
You’re not talking about the 90s anymore.
You’re talking about the 2020s.

You don’t get these years back.

Below are some of my favorite pics of me and from the 90's.

taplio

The Battle

Sean Gentry

Matt Ferguson

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The Battle

Sean Gentry

Matt Ferguson

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Sean Gentry's LinkedIn Performance

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