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’ve been to a lot of RKOs, and it’s easy to get fired up while you’re there, but it’s what you do when you come back home that counts. 

Lucky for me there are a few things that will keep the wind at my back walking into Docebo 

First is that there is already incredibly strong leadership. The biggest reason I took a bet on this company was the opportunity to work with Corey Marcel and Mark Kosoglow again. But I didn’t know at the time I would be fortunate enough to run the department with two incredible leaders in Jordan Harris and Steph Moran. The passion, empathy and awareness they bring the role and company has been remarkable. 

Second is the company and the product. I’m new to the space, but Docebo has such a rich history of being a category leader and delighting customers that it’s hard not to feel inspired. 



Coming into a new company, it’s easy to want to make your mark and change things. Make an impact. But the biggest thing I took away from this week is that change isn’t always necessary. Getting “rid” of things can often be a default for a new leader and can lead the team astray. 

Evolution is what we as leaders are here to do. Preserve what has made the company successful and evolve into the future. 


One of my favorite quotes is “fix the roof while the sun is shining”. And company off the biggest quarter that Mid Market has had in years, we now get to come back home, revitalized, and ready to put in the work (while it’s shining)


PS - Has there ever been a cooler RKO theme? Maybe I’m just a sucker for retro video games.

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

No alternative text description for this image

Here’s a marriage hack for you. 

No matter how tired or possibly even hungover you may be returning from RKO, never ever show it. Never. Ever. 

Follow me for more tips on learning things the hard way. 🫡

A 7 hour delayed flight was made a little better when I pulled this out of the front pocket of my travel backpack. 

My 8 year old sure knows how to send me off. 

Heres to my first RKO with the new company. 

So excited to be in person and kick off the new year! 

To Atlanta we go!

#Docebo #rko

I have hired over 100+ AE/SDRs in my career. 

For those of you looking to apply to a new sales role, here is some advice. 

Whenever I make a post that I am hiring, this is what happens

- I get hit with about 50+ DMs
- Of these 50 DMs...

- 90% of these just send me a message
- 50% send me there resume (which I can't process and don't have time to read through)
- 30% of these asked me to chat (As much as I would like to, I simply don't have 20+ minutes to speak with every person who wants a role)
- 10% actually sent me WHY they believe they are the right fit
- 5% are actually creative. They send me video messages, LinkedIn audio messages, etc. 

To put this into context, this is what your prospects face EVERY SINGLE DAY. 

90% of your prospects are just getting spammed with your offering and about 50% are asking to chat without knowing anything about you. 

A new job can potentially be a huge life change. 

How are you standing out?

Color coding my calendar helped me get promoted. And if you aren't, here is why you need to:

This created operational rigor on how I move through my week. 

We all joke that "its not happening if its not on your calendar" but in all seriousness, your weekly cadence determines your success.

I learned that instead of reacting to every slack message and random meeting request, you can take control by structuring your week into Value Blocks:

A Blocks: Your Highest-Value Work
B Blocks: Important, But Not As Critical
C Blocks: Valuable, But Can Be Flexed
D Blocks: Delegate And Empower

This is how I think about it each week:

Block your A Blocks first. 1:1s and prep time are untouchable.

Schedule B Blocks where they fit best but don’t let them overrun A Blocks.

Use remaining time for C Blocks, but be ruthless with prioritization.

Push D Blocks off your plate entirely.

----------

You need to run the week, or the week will run you. 

PS - Here is a quick snapshot at my calendar

Leaders, push your people to take care of themselves!

You can get burnt out pretty quickly in sales, especially if leadership doesn't encourage you to recharge. 

I was asked yesterday how I encourage my reps to actually do this:

Honestly, it caught me off guard but the answer is simple.

It comes down to 2 things:

First: It’s an expectation set by me. 

I’m clear about this early.

If you have been on my team, you likely have heard me say this ad naseum:

"You can’t give your best to customers if you aren't taking care of yourself"

So we talk about

- Blocking calendars to eat
- Taking real breaks
- Exercising
- Stepping away when needed

And every Friday, I ask them one simple question:

“How did you take care of yourself this week?”

Not as a nice-to-have but as part of the job.

Second: I do my best to model it myself

If leaders don’t live it, teams won’t believe it.

So I am hoping that my teams see me

- Prioritizing exercise
- Getting outside
- Talking openly about recovery (sleep, rest, meditation, etc)
- Protecting my own energy

Don't make it performative. Make it part of the culture. 

Here’s the belief I operate from:

Taking care of yourself isn’t separate from performance. It's part of it. 


That’s not a perk.
That’s leadership.


I am always striving to make my teams healthier. How are you doing that?

Recovery isn’t just for your body (although this sauna was the best purchase I made in 2025). 

You need to take time to recover your mind and emotional energy. 

Thanks to Apollo for this recovery kit with tea, candles and a Calm sub for a year. 

If you have reported to me, you know that I preach that  you can’t take care of customers if you can’t take care of yourself. 

So take the time. Recover. 

#apollopartner

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

Stop being lazy on your demos by asking "Does this make sense?" after you show something. 

Instead - 

Ask 

"How does this compare to what you are doing/seeing now?"

"How would this impact your business?"

"What are you seeing that you like or dislike?"

"Do you feel like this would help you achieve your goals? How?"

This simple change will inherently build a gap between current and future state and give you more insight into their process. 

Small fixes make big changes.

Go win more deals!

I've been promoted 4 times in the last 5 years. 

Getting promoted is tough. Tons of competition to move internally but I feel like I have cracked the code. 

Here is what I have done to stand out:

1. Hustle like a champ: Stay ahead of the pack. Soak up knowledge like a sponge. Don't simply rely on your company's enablement. Books, podcasts, you name it - then don't just sit there, put that stuff to work.

2. Get comfy with critiques: Your best growth lies in what you don't yet know. Seek feedback, take it in stride, and use it to level up your game.

3. Be your boss's go-to: Don't sit on the sidelines waiting for your turn. Get your hands dirty in the hustle. Lift some weight off your boss's shoulders. Learn as much as you can. Make your rise to the top a no brainer.

4. Be incredibly easy to work with: This doesn't mean saying "yes" to everything, but be coachable and adaptable to whatever comes your way. 

5. Crush your role: When that job opens up, you want to be the "no brainer", so ensure you are hitting your numbers while taking on more responsibility!

What else would you add that has helped you get to the next level?

"I'm getting 1x1'ed to death!"

Newer managers that I talk to feel like at the end of the day, they have talked to everyone and helped no one. 

The problem is that there are too many meetings and no time to think.

This creates constant context switching.

Here’s my uncomfortable truth:

It’s usually not the number of 1:1s. It’s that they’re being used for the wrong work.

If your 1:1s are spent on:

- Doing task updates live when things are out of date
- Pipeline walkthroughs
- Going over what’s already in the CRM

…then yes, they’ll drain you.

That kind of work forces constant context switching and keeps managers stuck IN the business instead of ON it.

Here is how you should think about your 1:1s with your reps... Focus on:

- Coaching how reps think vs what button to click

- Pressure-testing decisions before deals go sideways

- Removing blockers the rep can’t remove alone

- Building ownership. Helping them be the CEO of their book of business

If you leave a 1:1 more tired than when you started, you’re likely carrying work your rep should own.

The goal isn’t fewer meetings. It's better leverage per minute. 



Question for the seasoned leaders, what’s one thing you’ve removed from your 1:1s that made them more effective?

Less than 5% of salespeople at a new company take their first call without any training. 

If we wouldn't do this to a brand new AE or SDR, why do we continue to do it with our managers?

That is why most new managers are set up to fail on Day 1.

I see it everywhere.

Top rep gets promoted. Big win for the team! Huge expectations.

Then Monday morning hits. Sh*t gets real. Eight direct reports with endless questions. 

Zero preparation.

And what did we give them to succeed?

A title.
A Slack channel.
Maybe a book if we’re feeling generous.

The fact is that most SaaS companies promote people into management without ever training them to manage. 

Then we act surprised when:

Team performance drops
They work 60–70 hour weeks trying to figure it out
They question whether they even want the role and burnout shows up fast

Managing people is not an extension of selling. It’s a completely different skill set.

What new managers actually need:

1:1 frameworks that coach thinking!
Real feedback training 
Pipeline management systems that create clarity
Tools to have hard conversations without nuking trust
Time and energy management for managers, not ICs

And here’s the part most companies miss:

You don’t train managers after they’re drowning.

You train them before you hand them the role.

That’s how you protect your best people and build teams that scale.


 What’s one thing you wish you had been taught before becoming a manager?

This is how you should be thinking about creating pipeline if you want to hit over 100% every single quarter. 

You should be thinking about it in 3 buckets:

1/ Pipeline that helps you NOW - These are the deals that can move quickly. Deals that theoretically can help you get your number in this month/quarter. Champions from past companies that have purchased, older closed lost deals, etc. Rarer, but gold when you find them.

2/ Pipeline that helps you SOON - These are deals that need more education and should take 3-6 months to close. Will take more discovery, multi threading and ROI justification but will be necessary for your future quarters. 

3/ Pipeline that helps you LATER - These deals will close in 9-12 months. These can be some of your "bigger bet" deals, top target accounts. They need to be nurtured but you know they are the right fit and will eventually buy. 

This is meant to help you set expectations on who/when to reach out to. In actuality, you need all 3 to be successful long term and can change your prospecting strategy to fill each bucket. 

Bottom line, don't get discouraged by finding "LATER" pipeline. It all helps.

🔢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

Sometimes it takes longer than you think.

If you told Curt Cignetti back in 2008 that he wouldn’t get his first Power Five head-coaching job until 63, he would’ve laughed.

And he would have laughed harder if his only opportunity was Indiana.
The worst program in college football history.

But that’s what happened.

One of my favorite quotes ever is from Herb Brooks.
Coach of the 1980 US Olympic Hockey Team.

“Great moments come from great opportunity.”

You don’t know when your opportunity is coming.

Some people get theirs early.
Some people have to wait.
A long time.

But the people who eventually win?
They keep moving forward.

Small wins = Big Wins

My friend and fellow Hoosier Fan Greg Stanley sent me photo that last night.
Can't get enough of the coach Cigs Memes.

GO HOOSIERS!

People always ask me about going out on my own.
Because they want to do it.

My response is always the same.

What are you making right now?
What's your situation at home?

Because if you make a bunch of money
And your spouse/partner isn’t on board.

You don’t have a great shot of making it.

Thankfully for me.
My wife has a good business of her own.

And has always supported me.

Not once over the first couple of years was it:

Make more money or go get a job.
If it were, I prob wouldn’t have stuck through it.

Today is our 7 Year Wedding Anniversary.

Going out on your own is hard.
Doing it without support is almost impossible.

Small wins at home.
Made the Big wins possible.

Happy 7 years to my best teammate

I laughed at the situation below.
The truth is, I find it sad.

And I see it far too often.

Big Companies
Small Companies
Start Ups

It doesn't matter- I have horror stories for Days.

My biggest problem with the situation below.

No real data, plan, or path to get to the bigger number.
When noone hit the smaller number last year.

When you do this, your reps:

Have no belief and are demoralized.
Sending texts and talking behind your back.
And yes, probably looking for another job.

Your biggest job as a leader is selling your team.
Just like you used to sell your clients.

How did you do that?
You took them through a sales process.

What’s the problem?
How do we fix it?
Here is how we can do it.

It’s so easy to forget.
But if you don’t have buy-in.

You don’t sell anything.
The same goes for your team.

If they don’t believe
They won’t sell anything either.

What’s the “MAGIC” behind the biggest turnaround in sports history?
Here’s the answer every sales team needs to hear.

When the Hoosiers’ head coach was asked, “What’s the magic?”

His response was simple:
“There is no magic. It’s fundamentals.”
“A leader with a blueprint and a plan.”
“Create the intangibles: culture, mindset, philosophy.”

There’s no magic in sales either.
If you're wondering why your sales team is struggling, ask yourself if you have the things above in place.

My sales fundamentals have always been the same:
- Do we have the right people?
- Are we targeting the right accounts?
- Do we solve problems people actually care about?
- Is there a clear process from start to finish?

And the real differentiator:
Are you sticking to them and coaching them every day?

Will this guarantee the biggest turnaround ever?
No. But I guarantee it will create better results.

My dad has talked about the Rose Bowl my entire life.
Growing up in freezing Cleveland, it always felt unreal that it could be warm and sunny somewhere on Jan. 1st.

When Indiana made it this year, we finally went.
He grew up visiting his aunt in Bloomington and watching IU practices in the summer.

We watched one of the historically worst programs dominate a former powerhouse, 38–3.

Amazing what fundamentals can do.

Go Hoosiers.

You don’t have to Google him anymore.
2 years ago, very few knew who Curt Cignetti was when he said, “Google me, I win.”

Now everyone does, and the team he built will be studied by leaders forever.
He turned a team around so fast that some wondered if he was cheating.

How does he do it?

No 5 stars
Players who had been passed on
Fits the culture he was looking to build

One of the stars of the game last night was the WR Becker.

Kirk Herbstriet remembered him from high school.
“He was a solid player, but not highly recruited.”

He did not drop a ball this year and made every big catch last night.

I am often asked, what should I look for in salespeople.
My answer is simple:

“What type of culture do you have or are you trying to build?”

Then find some people who have had some success and fit the traits you want, then build them from there.

What it's not is go find “A players” (5 Stars) and hope they fit.
Why? Because I have found that “A players” often don't fit the way you want them to.

Indiana may be the best example of that I have ever seen.
Hopefully, we all learn from it.

Sales Leaders- If you micromanage one thing, MICROMANGE this.



YOUR LISTS

I learned this lesson years ago, when we created an SDR Team.

A couple of months in, the AE team was complaining.
So we looked at the meetings that were booked.

I laughed. I wouldn’t have run any of those meetings.
So I took a look at the comp plan.

They were paid the same for every meeting.
So they did what every sales rep does.
Took advantage of the plan.

Booked meetings that were easier to book.
Smaller companies that weren’t a fit.

Easy fix:
-Objectively define the ICP.
-Create the lists based on this.
-Pay them based on the quality of the meeting.

Problem solved.

A mutual complaint all sales leaders have when I first start working with them?

Our team closes too much of the wrong stuff.
There is only one person to blame.

-Objectively define your best accounts.
-Make it easy to understand why they are.
-And then hold people accountable to it.

And if you have to MICROMANGE- Do IT.
Everyone will thank you later.

Target the right accounts = closing the right accounts.

If you have hired a sales rep within the last year, you should listen to what Chris Mader says below in 64 seconds.

What I have experienced over the years is similar.
The mistake people make is thinking people should be better sooner.

It takes time!

Chris, Casey, and I talked for over an hour about all we have seen in 2025, working with over 50 Sales teams.

Topics Include:
- Why so many teams are missing quota
- Strategies for B and C Players
- Building a culture of Trust
- Understanding your reps and how they want to be led

If you want to hear more, links to Apple and Spotify are in the comments.

Hopefully, your customers don’t view your company like I view my Car wash.

A couple of months ago, my car wash changed names and ownership.

I never had any issues with the old one.
Every time I went to the new one, I notice issues:

-My car is soaking wet after going through
-Always a vacuum not working
-No clean towels

And the best part my monthly fee went from 15.99 to 24.99.

Yesterday, when I was about to go through I recognized the employee directing me in.

I asked, “Hey, you worked here before the name change, right?”

“Yes”

“Have people been complaining since the change?”

“Ya, a lot.”

“What’s the biggest difference?”

“The old one was family owned, and they cared; now we're owned by corporate.”

That was all I needed to hear.

The family owner cared much more than the corporate owner.

Leadership starts at the top.

Customers don’t feel ownership changes.
They feel standards slipping.

When leadership stops caring:
-Small issues pile up
-Prices go up
-Pride goes down

Culture shows up in the details.
Leadership always does.

A couple of things I wish I had known earlier in my Sales Management career.

25 Seconds to better discovery on your sales calls.

How do you stay top of mind, without being annoying?

A question I get asked a lot.

My advice is simple. Be different than everyone else.

A simple way I have used over the years.
And the text below is a perfect example of it.

Before the break, I had a meeting with someone.
We set the next steps, and I wasn’t able to make it.

And the next steps were never set after that.

Instead of hounding me every day to book the meeting, he used a tactic of mine without even knowing it.

He sent me a text about something else we had discussed.

I saw it and responded, and it reminded me of him without me being annoyed.

The timing for me just isn’t right at the moment.
But sooner or later it will be.

Salespeople have a bad reputation for always asking for something.

Differentiate yourself by not doing that.

Send something interesting about
-The Industry you are both in.
-Personal you may have learned about them.
-A topic that was discussed on the call.

And then don't ask for anything else.

You will separate yourself from all of the people “Checking in”
I can promise you that.

Bad Math leads to a Bad Path
It's why I always question it.

I have a new client who is starting a sales team.
He asks great questions on how we should judge them.

Without much data, it is hard to know.
He has done most of the selling.

The good thing is that he has good relationships in his industry.
Which means he can get some info.

When going through the math, I kept questioning one area.
He stood by it.

When we did the math, an A player could do over $1 million.

Which pumped him up, because it meant it would be easier to recruit top talent based on the commissions they could pay.

As I was still questioning the math, I received a text from him.
He admitted he had misunderstood the math.

Which cut the outcome by almost 1/3
Good catch, early.

Because bad math doesn’t just miss targets.
It creates bad expectations, comp plans, hires, and culture

Fix the math first.
Everything else depends on it.

You might be surprised by the type of REP that used to annoy me the most.

And it wasn’t the bottom performers.
It was the middle performers.

Yesterday, I listened to a client complain about a rep for a while.

When I asked where he ended up last year, I knew the answer.

“He hit his goal for the year.”

I understood why he said it.
He felt the goal was low.

Why, because the manager used to sell way more than that.

Here is what we forget.
Most people aren’t A players like we were.

Teams break down like this.

- Top Performers- Awesome Reps- 0-20%
- Middle Performers- Typical Reps- 60-80%
- Bottom Performers- Mess Reps- 0-20%

I have run my ATM exercise with clients for over 3 years.
Over 60 Times on teams from 7 different Countries.

I have never seen the %’s change much.

If you are frustrated all the time because people don't perform like you.
It’s gonna rub most of your team the wrong way.

Once you lose your team, your job becomes a lot harder.
Don’t be annoyed because people aren’t you.

If you would like to learn more about ATM
Send me a DM, and I can send you some info.

2 Types of Discovery Sales Reps miss too often.

Most discovery refers to pain.
And yes, we need to find pain to close deals.

Here are 2 others that are overlooked and also lead to more closed deals.

1. WHO ARE YOU TALKING TO?
Personality
Nice
Mean
Open
Closed
Tell you anything
Tell you nothing
Talks sports
Hates sports

You can usually tell right away.
And need to adjust based on who it is.

2. HOW DO THEY BUY?
Is it easy
Is it hard
What's their process
Who would be against it
Who wants it
Who else is involved
What's the biggest hurdle

Some are as much project managers as salespeople these days.
The more you know, the more you can navigate.

Don’t think of Discovery just as pain.
There is so much more to uncover.

Sales Managers- It’s the first week of February.
Ask yourself these questions about January.
(Reps, ask yourself if your manager doesn't.)

What did my reps do well?
What didn’t they do so well?
What obstacles can I remove?

What data do I have that supports the answers?

What can I do to help them get better?

Q1 will be over before you know it.
Don’t waste another day.

People will follow your lead if:

You make their lives easier.
Help them get better.

Small coaching conversations now

Beat big excuses later.
Lead early. Lead often.

Below is a classic mistake so many reps make.

I am not gonna lie, the $200 gift card was intriguing.
And the product could be something I need.

But like most LI spam messages, I have seen this one before.
Not even here to hate on it.

Just a lesson a lot of people need to hear.

I am not their ICP- Not even close.

Not only is it a waste of my time
It’s a bigger waste of their time.

The biggest mistake I see Reps make.

They want to sell everyone:
-They will be bigger someday.
-This will lead to something better.
-If we can get this ROI, they said they will spend more.

I have heard it all, and it rarely comes true.
And leads to so much wasted time.

Every second you spend on something that is not a fit.
You take time away for something that is.

Easy to say, Hard to do.
But is it the path to better deals and more success.

taplio

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Sean Gentry

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The Battle

Sean Gentry

Matt Ferguson

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Likes

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