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

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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.

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.

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The Battle

Sean Gentry

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