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.

First time Sales Manager, Long time Sales Rep | 4x President’s Club | 1x Founder’s Club | 1x Heavy Hitter

First time manager, long time sales rep. Approaching a decade @ HubSpot (am I a lifer?) 

Focused on being present in every zoom meeting and walk outside

Not the “idea” guy but always been entrepreneurial. I want a cool title and the experience of building or leading at a startup. For now I try to find ways to get that out of my corporate job via pilots or guinea pigging something new

Constantly thinking about consulting or coming up with a way to generate side income, but never actually falling through with it

AI won’t take my job…yet

If you want help with sales stuff message me

Brandon Kirsch

9 years ago today, I walked into the Boston HubSpot office with a huge black eye + broken orbital bone to start my career

(How I got that is a great story for another time)

Fresh out of college, I moved 1,500 miles 

My only sales experience:

- pretending to care about selling shoes at Sports Authority
- serving tables upselling crab-stuffed grouper at the Clam Bake
- and interning for one college semester at Gartner

I knew nothing about software

I actually thought HubSpot was GrubHub

Somehow, I landed as a BDR on the number one Small Business team covering the West Coast (Team Richmania, thank you)

The standards were high, and the legend of these sellers was already established

We're talking top logos won, multiple P Clubs, highest attainment, and the greatest accolade of them all...

a rock they found on a team hike that would go to the rep who closed the most MRR in a month

I immediately felt the pressure

Most mornings started by slamming 2 scoops of C4 pre-workout, where I'd be so excited to get to my desk that most of the time I wouldn't even get to the gym

Just sweaty, shaking, and frantically making cold calls in a 400mg caffeinated frenzy

Epic times

I got to listen to the best of the best 

Hear how they would battle competitors

Track how they won elaborate negotiations

Notice how they navigated a tough prospect

and grow from their harsh and direct feedback

I've always said most of my run at HubSpot has been because of that 22-year-old beat-up BDR foundation

3,285 days later, even though I have kicked the preworkout, I am still wired the same way

Excited to log on

Excited to build with my team

Excited to learn from all those around me

aaaaaaaaaaaaand I'm sure as hell excited to be less than a year away from my second Sabbatical! 

So here I am 9 years later grateful, thankful and only slightly blind in my right eye

Awesome

Senior Sales Manager @ HubSpot | 9 years | still figuring it out my way | getbyinsales.com (coming soon for now look at newsletter)

As a sales leader (really any people leader or founder) ask yourself one thing before you hit send:

“How would I react if I read this?”

More is not more when communicating with your teams

Your job is to absorb chaos and deliver clarity

So your offline comms should be:

           - short
           - to the point 
           - anchored in helping

If it doesn’t reduce noise…it’s adding to it IMO (even though you don’t mean to)

Don’t hide behind all the Slacks / reports

Handle it live

Another tactic that helps : I read on here a few months back to act like each word typed costs you $1. That works for me too

Sales Manager @ HubSpot | 9 years | still figuring it out my way | getbyinsales.com (coming soon)

Started a newsletter. First issue is about the one meeting I'd never cancel, even after getting my appendix removed

Link in comments

Work and my city collide at SXSW Austin this year with the HubSpot House

We want more registrants

So if you wanna shake hands and talk AI (or the end of SaaS), here is where:

"RSVP to HubSpot House during SXSW where enterprise leaders learn what actually works with AI: 

✨ HubSpot CMO Kipp Bodnar 
✨ AI Transformation Director Chloe Tambe
✨ Customer deployment stories with Patrick Damer, Arcis Golf 
✨ Technical workshops, panel sessions, and coffee chats all day 
✨ Surprise & delight inside of our SoHo house lounge

Drop in for a session or stay the whole day.

Limited capacity. RSVP today: https://hubs.la/Q043CXHZ0"

One day, maybe I'll get paid for posts like this

For now, it's for the love of the game

See you there

#HubSpotHouse #SXSW2026 #AILeadership #EnterpriseGrowth

Open article: RSVP Today | HubSpot House at SXSW by hubs.la

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The Battle

Sean Gentry

Brandon Kirsch

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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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