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.

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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.

Bob the Builder of Pipeline | Cold Calling Mercenary | Sales and Humor | Voted “#2 Best Parent” - by my 2 year old 🤷🏻

We can all agree that life is typically too serious and stressful, especially on a “professional platform”, so I enjoy breaking that norm with some laughter in both my content and sales process.

Professionally: I specialize in building and refining sales motions and top of funnel processes, bringing a unique twist that “breaks through the noise” of the modern day dreaded norm of what people believe is good revenue generation.

Before moving to Sales, I had the pleasure of coaching and treating thousands of clients through rehabilitation and personal training for almost 10 years, where I now channel the same energy and passion in leading GTM teams.

You’ve scrolled this far, we might as well get to know one another.

I’m a redneck working a white collar job living in a blue collar state 🥔

“When you turn a passion to a profession and truly love what you do, then you don’t work a day in your life.”

💥I’ve been lucky enough to do that twice💥


↙️“About me”↘️

Mission 1: To push past the “limitations” that your mind sets whether it be physical or mental.


Mission 2: To build my career in Sales and build a bridge between my old world of fitness and apply those principals to the business world.


- Constantly looking to learn. Go spark up a conversation and learn something about them and that little conversation could change your life. 

- “You don’t know till you try” I find to many people (myself included) stay comfortable and are afraid of breaking complacency.

- There is no greater feeling being coached or better yet, coaching someone else, and watching them succeed.

Eric Iannello

Saw everyone at Gong changed their title to Revenue Architect

…that’s cute

Voted ‘#2 Best Parent’ - by my 4 year old

A prospect has filed a restraining order against me

And I’m one step ahead of my competition because of it

You know what they say

If you aren’t flirting with the line of predatorial prospecting methods

You aren’t selling in 2026

I have a couple of accounts who are local to me so I’m prospecting them in person, hoping to make an impression that’ll lead to further conversations

Knowing my ICP pretty well and that the competition is fierce, I couldn’t rely on the typical brand merch to break through the noise…boring

So instead I found each potential champions home address and paid them a visit 


“Eric, wtf are you doing in my kitchen? It’s 5am”

Hey Stuart, I heard you liked your coffee with a kiss of milk from Snake River Farm cows. Tell me when to stop…

“Stop and GTFO!”

Boom, impression left 



Comment “milk” below for your free guide on how to prospect in 2026

Nothing makes me go “wtf did I do with my life”

More than being invited onto a podcast that’s only a glorified zoom call 
By a host who sits there and just nods in agreement 142x straight into the camera 
Because their ear bud cord restricts them from moving their head back far enough 
And hold a tiny mic they with their thumb and pointer finger which makes them look absolutely rediculus

“BuT We’rE oN SpOTifY”

That’s like saying you’re a best selling author on Amazon

So is my 13 year old nephew Susan

Don’t you love when job ads don’t disclose salaries

It’s like a game

Will this job allow me to live above the median income required in my city

Or and I trying to become a LinkedIn influencer and promote tools I’ve never used for a couple bucks per post






…buy Sybill

Congrats to literally every single company out there for forging a partnership with Claude

You should hang that award right next to your #1 G2 badge that no one else has…

I sell fleet safety technology to trucking and logistics companies across the country

On the weekends, I work horses

I’m a redneck living in a blue collar state working a white collar job

And there is two versions of me that show up on any given weekday

One is on a Zoom call talking dashcam AI and driver safety ROI with a fleet director somewhere in Louisville or Dallas

The other just finished feeding ducks and pigs before the kids started their school day at the kitchen table

Both are completely real and neither one would exist without remote work

I live in a community of ranches with neighbors who run a 1000 head of cattle

Guys who could fix a fence blindfolded but would think Im talking about a new model skid steer if I said CRM

There’s something grounding about spending all week in the weeds of enterprise sales and then Saturday morning hits and you’re working a colt and none of it matters

Your problems get real simple real fast when you’re the least important one in the arena

Now here’s the part that still tickes my toes

The same salary I’m earning from Netradyne

Would have kept us in a decent 2 bed apt somewhere in Dallas or Denver

Out here, it provides us a life

A real one

With land

With room

With a front porch that actually earns its square footage

A 1 bed in Idaho runs around $800 a mo

You know what that is in San Fran

The math isn’t even close

And the only variable that changed was the zip code…and the life with it


Remote work didn’t just give my family flexibility

It completely restructured what was possible for us

I think about that a lot because I talk to people every week who are grinding in cities that are quietly eating their paycheck from the inside out

Paying downtown prices to sit in a spare bedroom  then commuting 45 mins each way to sit on the same Zoom calls I am

The laptop doesn’t care where you open it

The deals close the same

The quota doesn’t know what state you’re in

LinkedIn loves to talk about work life balance like it’s some policy HR approves

It’s not

It’s a decision you make about where you live and who you surround yourself with

We made ours

A tight community of people who show up for each other

A dozen horses to keep me honest on the weekends

And a job I can do from anywhere that actually lets me be somewhere worth being


Remote work didn’t change my career

It changed everything

It’s hard to remember my life 5 years ago when I was just a PT, running a district of gyms and out-patient facilities 

Fast forward to what I’m able to provide for my family now

Definitely makes me better than you


…if people on LinkedIn spoke honestly

If I get one more rejection I’m going to do what everyone else does

…move into marketing

Dude, what in the holy sick season was that?!

Surprised we didn’t see a lock down mandate…


Sorry, too soon?

Do you remember when you created a profile on here

Felt like you unlocked a free source of information 

But then the more you scrolled 

The more you expanded your network

And the more you developed a community

The more you realized that if you don’t post selfies and exaggerated points of success with ChatGPT

The more you’re at risk for being blocked for creating content that may be considered a contrarian view to the “this is gold” standard 

Blocked by the same community of people posting AI-generated photos above life lessons they made up while cold plunging the one time

These are the “thought leaders”

Who preach authenticity above all but can’t create a thought without the help of the latest LLM and an irrelevant photo of themselves that’s been filtered by AI so much they’re hardly recognizable 

…but “hacks the algo” so they feed their fried dopamine receptors with false validation from people they’ve never met

The truth is like poetry, and everyone hates poetry

Couldn’t write it better myself

Actually, they couldn’t either

That’s kind of the point…

I see the same 5 influencers get their posts "Boosted" weekly

Which come to find out is like only $10 a week per post

But has any brand actually seen an actual return on boosting those very in-depth, highly technical, and clearly first person experience explanations?

Asking for a friend


...yes, I have friends




...no I don't pay them to be my friend

How I built a brand that towers over so many who fight to stay relevant

In every post I read, people love to over complicate what it takes to build a name that people remember on here

I broke it down into 4 easy steps

Step 1: poke fun at influencers who sold their soul to promoting brands and have turned into buy Sybil walking billboards

Step 2: criticize the overuse of AI in every piece of content they post where all the creativity is depleted and originality is a term forgotten

Step 3: find a topic that hits home to buy Sybil such as “the use of selfies” and build a campaign against the popularity of them buy Sybil so that you can leverage emotion behind the contrarian narrative

Step 4: stay consistent by not only leveraging your voice in posts but also buy Sybil in comments where it feels personal to the reader when you deliver the message and etch your name in stone

The complication isn’t in the execution

It’s that most think small and repeat what you perceive as successful

Foolish



The selfie section is where the emotion lives — that’s your contrarian hook that’ll get the comments going. Hiding Sybill in the post was a great idea to increase engagement. 

Would you like to see other options that you can post or did this give you what you need?

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The Battle

Sean Gentry

Eric Iannello

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Likes

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