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.

Building sales teams and delighting customers at early stage hyper growth startups.

Mike Gallardo

We're hiring AEs at Deel. 🥳

Here's why you should apply:

1. All remote. Forever and always. Work from anywhere in the USA or Canada.

2. The earning potential is real. I have reps hitting 200%+ consistently. More than 50% of the team hitting quota. The comp plan is built to reward top performers.

3. We promote fast. Promotion cycles every 3 months. I have already promoted 10+ people this year. And we're not slowing down.

4. You'll learn from the best. We listen to calls, coach every week, and genuinely care about your career growth.

5. We're still growing super fast. New products. New markets. New opportunities. The opportunities are endless.

If you're a hungry AE who wants to build something and get paid well doing it, this one's for you.

👉 Interested? Apply here: https://lnkd.in/gkhGnZdA

If you have any questions drop them in the comments!

Best of luck!
- Mike G

An AE on my team closed a deal that was dead for 45 days.

No responses. Ghosted. Done.

Here's what he did:

He didn't send a breakup email. 
He didn't drop the price. 
He didn't chase.

He sent one short message:

"Hey [Name] — I know the timing may not be right. No worries at all. In the meantime, here's one thing that changed since we last spoke: [specific update]. Is [priority] still something that's top of mind?"

That was it.

The prospect responded within 2 hours. 
Deal closed that Friday.

Most reps lose deals in the follow-up.
Not the pitch.

Because they either disappear or become annoying.

The best ones stay present without being desperate.
And they have a system for valuable follow ups.

That's the difference.

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

Most AEs send a follow up email after a discovery call that says something like:

"Great connecting today! I'll send over the info about X and looking forward to our next call."

That type of email usually gets ignored.

Here's what actually works:

Subject: [First Name] — Quick recap

Hey [Name],

Was great connecting today.

3 things I took away from our call:

1. [Their #1 priority in their words]
2. [Key challenge they mentioned]
3. [Something specific they said that matters]

Based on that, here's what we'll cover on our next call:

[Describe the demo/next step — 1 sentence on what you'll show and why it's relevant to them]

Looking forward to connecting at [Day] at [Time].

— [Your name]

Super clean and focused on them and how they will benefit.

The reps who win send emails that make buyers feel like they were actually listened to.

Bonus: That email does it in under 30 seconds to read.

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

graphical user interface, text, application

The best AE I've ever managed didn't have the best pitch.

Wasn't the most polished on calls.

Wasn't even the loudest in the room.

Here's what she had:

She treated every lost deal like a lesson and every won deal like a system.

When she lost: 

She reviewed the call, found the moment it went sideways, fixed it.

When she won: 

She documented exactly what happened and repeated it. 

Even looked for ways to make the process and experience better next time.

Most reps do the opposite.

They move on from losses fast and treat wins like they were meant to happen.

So the gap between average and elite isn't talent.

It's the work someone puts in after the deal is done (win or lose) that matters most imo.

That's where careers are built.

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

Most reps panic when a prospect says "I'm not interested."

Here's what to do instead:

Don't argue. Don't pitch harder. Don't cave.

Just say: "That's actually why I called." A strategy I learned from the one and only Jeb Blount 

Here's how it plays out:

1. "Not interested." → "That's actually why I called. Most [personas] I speak with feel the same way until they hear how we helped [similar company] solve [specific problem]. Mind if I take 30 seconds?"

2. "We already have something." → "That's actually why I called. [Company] was in the same spot and found we could [specific differentiator]. Worth a quick look?"

3. "Not the right time." → "That's actually why I called. Most of the best conversations I have start that way. What would need to change for the timing to be right?"

The magic of this phrase:

It doesn't fight the objection. It works with it.

The prospect expects you to fold. When you don't (in a nice, conversational and clear way) they get curious instead.

It's one of the most simple ways to overcome objections. 

Give it a try and let me know how it goes!

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

One of my best AEs has a 39% win rate 🤯

Her secret is one question she asks on every single discovery call:

"If you could change one thing about how your team handles [process] right now, what would it be?"

That's it.

Here's why it works:

It's specific enough to get a real answer. 

Not "what are your challenges?" which is pretty vague, and tends to get vague answers (unless you're lucky).

This questions forces the prospect to prioritize. 

Suddenly they're telling you exactly what matters most.

The answer tells you everything. 

And gives you exactly what you need to position your product as how to best solve what's most important to them.

Most discovery calls fail because reps ask broad questions and get broad answers.

They leave without knowing the #1 thing the buyer actually needs to fix.

Ask the one question. 
Listen hard. 
Build everything else around the answer.

That's how she closes 4 out of 10 deals.

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

I use AI every single day.

And in my opinion, Claude is the strongest AI tool for sales right now.

Here's one of the easiest ways to start using it:

Track your closed won deals every month. 
That's it.

Just log how many deals you close each month. 
One number per month.

Then drop that data into Claude and ask it to visualize it.

What comes out the other side? (See image below 👇)

A clean chart. 
Month over month trends. 
Automatic callouts on what's working and what's not.

This took me < 1min to make.

Now take that into your next 1-on-1 with your manager.

I promise, nobody else on your team is doing this.
And that's exactly the point.

AI isn't going away.

The reps who figure it out now are going to make more money, get promoted faster, and be a lot harder to replace.

The best part?

You don't need to be a tech person to start.
You just need to start.

And this is one of the simplest first steps you can take.

What are you waiting for?

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

70% of my team hit quota in 2025 🥳

And 80%+ hit quota in both Q3 and Q4.

I'm incredibly proud of this team.

Here's why I think we're built different:

1. The best product on the planet.
Deel is the #1 global HR and payroll platform. We were built for global teams from day one. It's a fundamental advantage that makes selling easier and customers a lot happier.

2. Coaching and training that's actually dialed in.
Our managers are top tier. Our reps are world class. When you join this team you are surrounded by greatness every single day. There is no better place to sharpen your skills and grow as a seller.

3. Leadership that genuinely cares.
Every manager on my team makes time to listen. We take feedback seriously. We move mountains when we can. You will never feel like just a number here.

The reason we're hiring right now? 
We've promoted so many people internally that we're backfilling a ton of roles.

That's an awesome problem to have if you ask me :)

If you want to sell an incredible product, get coached up, hit quota, and build a real career, there's no better place than Deel.

Interested? Apply here: https://lnkd.in/gkhGnZdA

Best of luck!

- Mike G

She was at 175% of quota.

Working a deal that would've put her at 274%.

Contract was out. Deal was in commit. 

But then a week went by with no response from her champion.

She wasn't panicking.

And the reason why comes down to something we coach all our AEs on from the very first call.

Multi stakeholder discovery.

3 key questions:

1. "Who else on your team would benefit from seeing how this works inside Deel?"

2. "I noticed [name] is on your finance team. They usually like to get involved when we get to commercial terms. Would you be open to including them on our pricing call?" 

3. "I'm really excited about the potential partnership here and helping you with [key business initiative]. As we get closer to pricing, do you mind walking me through your internal process? Who's typically involved, what do they care about most, and how do they like to be included? That way I can make sure I'm giving you exactly what you need to present this internally." 

The third one’s my favorite. 

It’s a bit longer but it’s great for mapping the people, the process, and the timeline early. 

That way you’re ready if a situation like this one ever pops up.

So when the champion went dark.

She had a couple options:

1. Call her (tried this already but no luck)
2. Go over her head (do not recommend!)
3. Loop me in

She decided to loop me in because a leader to leader message would hopefully cut through the noise and get a response. 

First we had to make the message as targeted/relevant as possible.

We use Aligned (which automates deal insights) and noticed the CFO had not reviewed the pricing yet. So that was probably what was holding the deal up.

So we crafted a targeted message to her champion about getting the CFO aligned on pricing, got a response the next day, and were able to get the deal back on track and moving forward.

Without the right insights this deal could have very easily stalled out.

That’s why every complex deal our team runs lives inside Aligned. It gives our AEs total visibility into what's happening inside the account when they're not in the room. 

That way, AEs can take targeted and effective action (like she did) to keep momentum going. Especially when things slow down or champions go dark.
That level of visibility literally makes or breaks your most important deals.  

👉If you haven’t already I highly recommend using it for free here: https://lnkd.in/gqNS6GRW

And if you have any questions let me know in the comments!
Always happy to help :)

- Mike G

#alignedpartner

Brand partnership • Sales Director at Deel

90% of my team hit quota in Q4.

Here's how we crush it with discovery.

Instead of asking questions like:

"If you could wave a magic wand, what would you change?"

or...

"If you don't do anything about this, what happens to the business?"

Which are somewhat awkward and unnatural, and sound like you're trying to manufacture urgency.


Here's the type of questions we ask instead:

1. "I work with a lot of [role]s and they're usually focused on one of two things: [priority A] or [priority B]. Is that the case for you, or is something else more top of mind?"

2. "What's going on in the business that's making this a priority right now?"

3. "Can you walk me through your current process for [X] step by step?"

4. "When it comes to [challenge they mentioned]. Can you share a specific example of when that's been a problem?"

5. "If this call goes well and we end up working together. What would need to be true for you to call it a success 6 months in?"


The difference between good and bad discovery questions isn't how clever they are. It's whether they sound like something a real person would ask.

And that they're focused on real priorities, problems and processes they have. That way, you can center your entire sales process on how you'll help and how your solution is better positioned for their business vs competitors.

What's your favorite discovery question?

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

taplio

The Battle

Sean Gentry

Mike Gallardo

Followers

Posts

Engagements

Likes

Performance ScoreSean Gentry's LinkedIn Performance

Performance ScoreMike Gallardo's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Sean Gentry

Mike Gallardo

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

Performance ScoreMike Gallardo's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreSean Gentry's LinkedIn Performance