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.

Salman Mohiuddin

Enterprise Account Executive, Marketing Cloud (Financial Services)

Helping sales pros + teams build healthy pipeline to close more deals faster | Sales Coach + Trainer @ SSA | 17 years as a quota carrier | ex-Salesforce, Asana and IBM | Interview Ace

Problem before Product. 

17 years of tech sales experience as an SDR + AE at Salesforce, IBM and Asana all as an individual contributor. There’s more 👉

Currently Founder at Salman Sales Academy.

#1 Sales Influencer in Canada 2025 (source: Favikon)

Coaching and training AEs, SDRs, BDRs + sales teams to find and close more deals.

Started as an SDR in 2006, moved to AE in 2007.

6 years at IBM
- SDR 
- SMB + MM AE
- small Enterprise AE

7 years at Salesforce
- MM AE (new logo)
- Enterprise AE

2.5 years at Asana
- Enterprise AE 

2 years at startups 
- SMB AE (new logo)
- Enterprise AE

I currently coach + train AEs, AMs, BDRs, SDRs and Sales teams on prospecting, problem enablement, discovery, demos, deal strategy and interviews.

DM me for:

- 1:1 Sales coaching 
- Sales team coaching + training for your company
- 1:1 Sales interview consults to help you land an offer
- Speaking engagements or sessions for your company
- Podcast guest 


✅ Widely recognized as a master prospector & hunter

✅ Experienced in consultative selling to C-level, Information Technology (IT), Marketing, Ops, HR and more.

✅ Sales Interview Ace - the interview playbook I've built has resulted in an 80% success rate in interviews

✅ Possess an Honors B.A., Economics

[Sales COACHING]

➡️ Problem Enablement [build confidence in truly understanding your persona and the problems your solution solves for]

➡️ Prospecting [cold email, cold calling, warm calling, objection handling]

➡️ Discovery [full 5-step discovery framework to help lead your calls with confidence and in the flow of the conversation]

➡️ Demos [full demo framework, engaging demos, justifying spend, taking control of deals, PoC/Pilot strategy, etc…]

➡️ Deal Strategy [multithreading, uncovering power, executive alignment + engagement, quantifying pain, business case, negotiation, dealing with objections throughout cycle, taking control of your deals, champion building, mutual plans, forecasting, etc...]

➡️ Interviews - I've refined my interview playbook that has help 80+ folks land offers [interviews, mock cold calls, mock discovery, mock presos, territory plans (that will wow a hiring manager)]

I've built an entire Sales playbook from prospecting to close in everything in between based on my 17 years of experience as an individual contributor in tech sales.

No fluff. All actionable sales insights and content, with real examples, that you can start using right away in your role and see immediate results.

Check out the coaching programs and testimonials here:  www.salmansales.com

or DM me. Happy to help.

Founder

Helping AEs, SDRs + Sales teams find and close more deals. 🚀 Boosting income and revenue. 

17 years of tech Sales experience, all as an individual contributor. I've been in your shoes as an SDR, Commercial, and Enterprise AE at companies like Salesforce, IBM and Asana. In the trenches. Exceeding targets. Even in economic downturns.

Documenting all of my learnings, I've built out a Sales playbook. Now I want to give back to YOU.

I teach individual contributors + Sales teams on how to sell better, exceed targets, boost income / revenue, and accelerate growth. All with actionable Sales content and insights that you and your team can start using right away. Seeing immediate results.

Spoke to an AE who ranked #2 globally out of 700+ AEs at his company last fiscal.

He’s gunning for #1 this fiscal (which ends in a few months for him)

What’s he doing differently?

It’s not complicated.

It’s the fundamentals.

(and it works)

Here’s a glimpse 👇

1. Knows the problems inside and out

He got the same product training as everyone else during onboarding.

Rather than jumping into product after hearing an ounce of pain, he takes a problem-first approach when speak into IT security leaders.

He spent his first few weeks in role truly understanding not the product, BUT

→ the problem it solves (in prospects language)
→ how said problem affects each key persona
→ how typically teams tackle the problem today
→ negative impact of ignoring the problem
→ KPIs + metrics affected by problem 

So when he talks to prospects, they think:

“This person gets my world.”


2. In discovery, he goes beyond surface-level pain 

If you took him aside and asked him about an in-quarter deal, he could tell you:

→ the specific problem they are facing (in their language)
→ how the team is dealing with problem today 
→ the use cases tied to that problem 
→ the impact on persona, team and org
→ who it’s affecting and why it actually matters
→ the exeutive priority that problem puts at risk
→ the risks or obstacles currently in the deal 
→ how he’s proactively de-risking them
→ next step, who owns it, and the goal

He knows discovery isn’t a stage in the sales process.

It runs throughout the entire deal cycle.


3. He leverages his x-functional team

Works closely with SDR, SE, CSMs, Pro Services, and a TON with partners.

But he doesn’t just “loop them in”. What he does:

→ prepares SEs before every call and demo
→ brings in execs for exec-to-exec alignment
→ sends each exec a 1-page deal brief before that 
→ works with partners as a true win-win
→ consistently meets with them, “walks the halls”
→ builds mutual plans that hold everyone accountable

………………………………………………

I’ve been coaching this AE for almost 2 years.

He wants to Finish #1 globally this fiscal.

……………………….

With how competitive the market is.
With budgets being super tight.
With all the AI tools at our fingertips.

IMO, it comes down to the fundamentals of sales that will help drive our success.

Helping Sales Pros Close More Deals + Crush Quota | 17 Years as an AE | ex-Salesforce, IBM + Asana | Founder, Salman Sales Academy | #1 Sales Influencer in Canada 2025

1st year AE, I was told these were good disco questions:

“Do you have budget set aside for this?” 
“What’s your timeframe in making a decision?” 
“Who's the decision maker on your end?” 

😐 

I asked them pretty much exactly like that. BANT style.
And prospects saw right through it.

They felt lazy.
Salesy.

Pure “check-the-box” questions.
Deals didn’t move forward.

Conversations stayed shallow.
Something had to change.

If I wanted real answers, I had to stop qualifying and start understanding.

Here’s what changed everything 👇

4 simple shifts that made qualification feel natural 
(not salesy)

1. Timeframe → Consequence

Instead of asking:
“What’s your time frame?” 😐

Ask:
“What’s happening today that’s causing you to take a closer look at this problem now vs later?” 🙂

Now timing had meaning.


2. Decision maker → Initiative ownership

Instead of asking:
“Who’s the decision maker?” 😐

Ask:
“When folks are trying to solve a big problem like this I find it’s usually driven by someone at the exec level. In addition to yourself, is there an exec on your side this initiative is being driven by?” 🙂

No pressure.
Just context.


3. Budget → Reality check

Instead of asking:
“Do you have budget?” 😐

Ask:
“Usually what I find is companies fall in 1 of 2 buckets:
a) have budget set aside for a specific project + eval
b) there's no line item for fiscal aligned to the project + eval
Which bucket would you put yourself in?" 🙂

Way more honest answers.


4. Sign-off → Risk

Instead of asking:
 “When do you expect sign off?” 😐

Ask:
“What would prevent your CIO and CFO from moving forward?” 🙂

Obstacles surfaced early.
Not at the end.

............................................

The difference?
Purpose.
Intention.

Respect for the buyer.

Ask questions that help prospects think, not questions that make them feel sold to.

Not so hot take: Quit wasting time and team resources on RFPs you have no business being in.

Imagine this 👇 

→ prospect invites you to participate in an RFP 
→ AE drops what they're doing, pipes a 100k deal
→ gathers team resources (SE, PS, Product, etc...)

Team is heads down for the next few weeks.

Responding to the 100+ questions.

Preparing for the demo so they can meet req'ts.

Only to find out a month later they aren't the selected vendor.

.................................................

Here's why this is a mistake:

→ you're late to the party if you just found out about the RFP
→ prospect already has a good idea on the vendor
→ your team wastes weeks on a lost cause
→ resources are drained

Winning RFPs requires early engagement.

Ask yourself:

- were we engaged prior to release?
- did we help co-create or shape the RFP?
- are they willing to meet so we can learn more?

If not, you've got to make the smart decision and walk away

... and focus on winnable deals instead.

(There are exceptions here, especially in gov't / public sector for example where RFPs are the norm)

But in the majority of cases, it's true.

Use your time (and your team's time) wisely.

The best salespeople know when to say no.

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The Battle

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