Webflow

Sr. Manager Corporate Sales

pclub.io

Course Instructor and Founding Member

Outbound Squad

Coach

Pavilion

Course Professor - Front Line Manager School
Completed - Rising Executives School

Member and Course Instructor

Catalyst Software

Customer-Led Growth Advisor (CLG)

First Round Fast Track

Mentor

Outreach

- Created and scaled the Growth segment from 6 to 25 reps and 4 managers, globally 
- Created playbooks, processes for AEs, managers in role
- Oversaw global sales - achieved 130% NRR and 125% to quota
- Top performing team in revenue % to quota in 2021

Director of Sales

- President’s Club 2021
- Top performing AE team in SMB for 2020 (% to quota)

Sales Manager

Zillow Group

General Manager, Enterprise Sales

Sr. Manager, Enterprise Sales

SnackNation

Enterprise Manager

Agent Image

Sr. Account Executive

Coaching Frontline Managers To The Next Level | Sales Leader @ Webflow

I have led 5 different sales teams at all levels (SMB through Enterprise) and am now on a path to help new sales managers. 

What I believe in - 
1. Creating and maintaining a great culture of growth and accountability
2. Understanding numbers and creating predictable forecasting
3. Fostering a high performing team that breaks records
4. Supporting individuals to become better versions of themselves personally and professionally
5. Incorporating health and wellness to drive performance 

Past -
1. Grew a SaaS business 10x in ARR (Outreach.io - Now doing it at Webflow)
2. Hired and trained 100+ AEs, 20+ managers 
3. Built and led onboarding/enablement programs around management

If you want to get better, I can help.

Do you have a big interview coming up for a job that you really want? 
 
This could be literally life changing.  
 
Please, please, please do these things: 
 
- Go the person's LinkedIn that you are meeting with 
- Look at where they live, what role they are in, the length they have been in that role, if they have been promoted 
- Write key notes down for talking points  
 
Then: 
 
- Draft a quick email preparing that person for the interview 
- Share who you are, why you are meeting, and why you are the right person for that role 
 
Please, please, please treat this interview like a top deal you are trying to win. 
 
Tired of seeing people wing it in meetings that can literally impact the next 3-5 years of your life!

Sean Gentry

I Help Coach Sales Managers To The Next Level | Leader @ Webflow

What should I include in a pre-interview email?

How can I effectively research the interviewer on LinkedIn?

What are some tips for preparing for a job interview?

The quickest ways to upgrade your demos - 

Stop asking "Does this make sense?"

Instead - 

Ask "How does this compare to what you are doing/seeing now?"

This simple change will inherently build a gap between current and future state and give you more insight into their process. 

Small fixes can make big changes. 

How can demos be enhanced for better engagement?

How does creating a gap between current and future state impact demos?

Why is gaining insight crucial in demo presentations?

I believe I have cracked the code on getting promoted internally - 

Every role I have been in from SDR to manager, I have been promoted in less than 2 years.

𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝘀𝗲𝗰𝗿𝗲𝘁 𝘀𝗮𝘂𝗰𝗲 𝘁𝗼 𝗰𝗿𝗮𝗻𝗸 𝘂𝗽 𝘆𝗼𝘂𝗿 𝗴𝗮𝗺𝗲.

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?

What are some strategies for getting promoted internally?

What are some recommended books for professional development?

What are some recommended podcasts for professional development?

Want to know how my best closers are finishing their demos?

The last 5 minutes of your demo is the perfect time for a soft close. 

It's also your opportunity as a seller, to confirm that you are spending your time in the right place. 

Here is what this sounds like:

*You are wrapping up the demo*

"Was there anything that you wanted to see but didn't as we wrap up here today?"

"Was there anything that you saw that you didn't like?"

"We will get to pricing, but based on what you have seen so far, do you believe that we can help you solve for XYZ"

Without these questions, we go too quickly to pricing without even knowing if our prospect is SOLD.

This also gives us the opportunity to back up if we have missed something crucial. 

So, don't rush past these last 5 minutes. 

Slow down to speed up. 

How can a soft close be effective during a demo?

What are some best practices for sellers during demos?

How can sellers ensure their prospect is sold before discussing pricing?

"I don't want to be pushy" - One of my top reps said to me once 
 
It's pretty obvious - you shouldn't be "pushy" 
 
You shouldn't try to persuade anyone.  
 
Instead, you should ask questions to see if you can help them. 
 
If they agree they have a problem: 
 
- Find a solution 
- Prove how well that solution will work for them 
- Agree that this solution will be the best route for them to help them achieve their goals 
 
No pushing. 
 
Just educating.

How important is client education in sales?

What are some tips for successful sales reps?

A few months started ago, I phrased a new acronym with my team when things were going "too smoothly"- 

N.C.W.F. 

“No commission without friction”

This is a sure fire way to get blindsided at the finish line. 

It was becoming a common theme in all of the deal cycles that I am part of.

--------

Buyers are afraid of buying the wrong platform. 

Stakes are too high. 

Their jobs are on the line. 

So while they may be researching your product, friction is inevitable. 

What does this mean?

Examples of friction we are seeing:

- Budgetary concerns 
- Billing concerns 
- Timing concerns 
- Competition in deal cycles 
- Product or feature gaps 
- Stakeholders that are involved but you can’t speak to 

It’s your job as a seller to suss out these issues early in the deal cycle. 

That way you can address them and get around them before it derails your deal at the 1 yard line. 

My advice?

Ask the questions you sometimes don’t want the answers to. 

Go into the storm head on. 

Search for friction. 

No. Commission. Without. Friction. 

NCWF

How can encountering friction benefit deal cycles?

What role does friction play in deal success?

What challenges do buyers face in deal cycles?

I hear from sales managers that they have trouble finding top talent to hire. 

At the same time, almost none of them are building a strong personal brand on LinkedIn 

I have found a good amount of candidates from them reaching out to me on this platform. 

Over time, this figure is set to rise. 

All because branding has a compounding effect. It's a long-term game.

It takes 15 minutes a day. Post about who you are, what you care about, why someone would want to be on your team. 

Don’t wait for change - be the change.

Why is building a personal brand on LinkedIn important for sales managers?

What are some best practices for building a personal brand?

How can LinkedIn help me build my personal brand?

Was up to almost midnight yesterday working with an overseas client to get a Docusign in. 

This deal would have helped my rep pass quota and add to our great Q1. 

We needed it by 12pm. 

Got it at 12:50am. 🤷🏼‍♂️

If that’s not SaaS sales, I don’t know what is. 

Now let’s go have a fantastic Q2!

How important is dedication in SaaS sales?

What significance does Q1 hold for businesses?

What potential does Q2 offer for business growth?

If you don't have one already, I would add a "Kudos" folder to your desktop. 

This is a folder filled by you, to help you. 

Here is why this is a no brainer:

- Whenever you are up for review
- Whenever you are trying to move up in your company
- Whenever you are applying for a new role

You need social proof. You need people complimenting you. You need people saying what an amazing teammate/employee you are. 

So here is what you should do:

- If you get a shoutout from your teammate or boss, take a screenshot
- If you get an amazing customer email complimenting your skill, take a screenshot
- If someone shouts you out on LinkedIn, take a screenshot
- If you overachieve your quota, take a screenshot 

All of this proof will help you build credibility and anchor to your worth. 

No one is too big to take a screenshot of kudos. 

Start one if you don't have one. 

What is the significance of social proof in career advancement?

How can a 'Kudos' folder benefit professional growth?

What role do kudos play in promotions within a company?

The simple truth about creating pipeline if you are an AE - 

You should be thinking about it in 3 buckets:

1/ NOW pipeline - 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/ SOON pipeline - 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/ LATER pipeline - 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 guide 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. 

Happy hunting!

What are the key strategies for Account Executives?

How significant are LATER deals for long-term success?

How important are NOW deals for sales success?

When I was a new manager, I was so consumed by fixing EVERYTHING. 

I would look for things that weren't working, and drove myself mad by trying to change it. 

Then I learned that I was approaching burnout. And that sometimes, its not worth going there. 

Let me explain...



Too often I see new managers trying to only fix what is broken.

They see a rep who is doing all of the activity but not producing. 

Instead- 

Dissect the wins. 

See what IS working.

Analyze the best rep - the top. Who is doing it better than anyone else?

Take their process, their prospecting, what they are doing OFF the phones.

Make a blueprint.

Document it. 

Hand it to your ramping reps and the ones struggling.

Once they start to adopt, analyze, iterate.

Scale down instead of trying to fix the bottom and scale up.

What are some common mistakes new managers make?

Discovery calls are like a first date. 

If you go in swinging with the "tell me all of your challenges" in the first two minutes, its like asking "tell me about your childhood" or "do you have a good relationship with your parents?"

So go in slow. Ask simple questions first as you build trust.

Or trust me, there won't be a second date. 

How crucial are discovery calls in professional interactions?

Why is building trust important in business conversations?

What parallels exist between discovery calls and first dates?

The feeling when - 

You wake up with a surprise double album > You wake up with a signed Docusign

#TTPD

To be truly great at cold calling, you have to be great at objection handling. 

Here is the best framework to use:

1/ Empathize - Most prospects expect us to take their objection and hang up. 
2/ Validate - Our validation of their objection can disarm our prospects.
3/ Offer - Stay in control with asking the right questions to offer a path forward.

Here is what this sounds like in practice - 

Prospect: "I'm not interested"

Me: "I get it, and sounds like I may be off here. Usually people in your role are struggling with XYZ. Is that something you run in to or is everything perfect there?"

------------

Using a strong framework in your outbound objection handling can help you navigate past the first "no" and lead to more meetings! 

What is the best framework for objection handling?

What are some best practices for outbound objection handling?

How can you offer a path forward during objection handling?

I'm not perfect. I sometimes make poor decisions.  
 
But there is one thing that has helped me maintain trust with my team and promote the culture I want -  
 
It's asking reps: 
 
"What would you change about this process?" 
 
See, I try not to ask "What do you think of this process?" 
 
As that will promote a "its fine/good" - Aka agreement without criticism.  
 
Seek to improve. Engage your team for feedback.  
 
More often than not, the best answers come from the people engaging with your customers head on.

What is the significance of trust in team dynamics?

How does feedback contribute to team growth?

Drake and Kendrick are putting on a masterclass of researching your prospect. 🤯

SDRs and AEs, listen up!

How important is prospect research in sales?

What are the key responsibilities of SDRs?

There is nothing more important than your 1:1 each week with your manager. 

But here is the truth...

Most  managers and reps “wing” their 1:1s.
 
Not having a plan = planning to fail 
 
Managers go into the meeting and say “so.. what’s up?” 

So here is how we can fix this - 
 
Block specific time for 1:1 prep. 
 
Scheduling a 30-45 min block to dig into 1-2 reps (per session) look at a few things: 
 
- Month/quarter to date performance 
- Activity metrics 
- Recent calls in gong / activities on deals 
- Pipeline cleanliness / health 
 
These checks which can take minutes normally help you assess WHY you are succeeding or struggling. 
 
Go into a 1:1 knowing where to steer the meeting and what to land on. 
 
Having a plan helps you achieve a tactical outcome. 
 
So, take the time. 
 
Prep for a 1:1 like you would a sales call.

How can effective 1:1 meetings benefit professional growth?

What are the key responsibilities of a manager?

Why is preparation crucial for successful meetings?

There is no "silver bullet" cold call script

But here is my favorite framework that I have seen work most often:

"Hi X, this is Sean from Superbiz. What did I catch you in the middle of?"

(Gets ahead of the objection - "I am in a meeting" / "I'm picking up my kids from soccer practice" etc)

"Well, I appreciate you picking up especially from a number you don't know. I'll be quick. There is a reason I call you, mind if I take 15 seconds to tell you why?"

(Permission based opener)

"I'm working with several (their role) in your field and they tell me they are running into X, Y, Z (problems). Are you seeing that or am I way off base here?"

(Problem based discovery with a potential OUT for them if I am off base)

"Totally get that. Is it fair for me to quickly lay out how we can help? If I'm still off, then I'll go kick rocks"

(Hopefully gets a laugh and the ok to build intrigue)

"When these people work with us, they see X, Y, Z - does that resonate with you?"

(If so, move to booking. If not, its either the wrong fit, or you need someone else at the company) 

----------

The ultimate goal here is not ALWAYS to book the meeting but to gain information. 

If you learn that they are the right fit - Awesome

If you learn that they aren't the right fit - Good, move on or find another contact. 

The goal is always information. 

What else have you found that is working right now? 

What impact does a well-structured cold call script have on client engagement?

How can gathering information be more valuable than booking a meeting?

Curious - 

You are an AE and get an inbound lead (or a call set for you by SDR). What do you do before the first call?

Hit me in the comments with what you believe should be "best practice"

What are the key responsibilities of an Account Executive?

What are some common best practices for handling inbound leads?

How important is it to prepare before engaging with an inbound lead?

"Dont dwell on the past"

Fair. 

Butttttttt retroactively looking back at your past has to be one of the greatest drivers of change. 

If you are a rep or a manager and not looking back at your week, month, quarter - you are missing out. 

On a weekly basis:
- Did I hit my metrics? Calls/emails/meetings
- Did I hit my weekly quota?
- Did I move each account forward?
- (Subjective) What wen't well? / What didn't go well?

On a monthly basis:
- Did I hit my monthly metrics?
- Did I hit my monthly quota?
- Did I create enough opportunities?
- (Subjective) What do I want to continue doing? / What do I want to stop doing? / What do I want to START doing?

Also run for the quarter. 

Blocking time for this every Friday has been a game changer to go into the following week/month/quarter. 

Always stop and look back to create a better future. 

What are the key responsibilities in sales roles?

How important are performance evaluations for professional growth?

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