👩🏻‍🏫 Krysten Conner

krystenconner.com

--> Pressure to hit your number got you lying awake at 2:41am?
--> Stressing over deals that are ghosting or slipping?
--> Burned out & feeling major anxiety?

Empowering tech sellers to close more complex deals is what drives me.

I spent 12 years in Enterprise sales as an Account Executive with multi-billion dollar tech companies like Salesforce, Tableau and Outreach. Along the way, I blew past performance goals in multiple roles.  Doing 14X what anyone had done in my territory, being #1 in new logo acquisition, and achieving a 47.6% win rate.

It wasn't always like that, though.

Early on, I couldn’t confidently qualify deals in or out quickly. I wasted lots of time on deals that didn't turn out to be real. My discovery felt haphazard, and I struggled to get prospects to go in depth or quantify their pain.

My first sales cycles were some of the longest on the team. Deals frequently slipped, and I got ghosted a lot. All which I felt powerless to change. I was always waiting for the customer. I didn’t know how to lead so buyers wanted to follow.

You might relate to feeling like I did: burnt out, anxious, and like you don't belong in sales. The sad part is feeling behind, scattered, and overwhelmed has become the new norm.

It took me over 10 years to gain the confidence, knowledge and skills that I needed to be a consistent top performer.

My mission is to ensure you get there faster - by sharing what I’ve discovered throughout my 12-year career.

My content and training has been featured by: 
--> pclub / Chris Orlob
--> 30 Minutes to President's Club
--> Kevin Dorsey / Live Better, Sell Better
--> Sell Better / Daily Sales Show
--> Outbound Squad
--> Challenger
--> Vidyard
--> RepVue

Here’s what my clients say: https://www.linkedin.com/in/krystenconner/details/recommendations/

--> Sign up for my newsletter for weekly coaching in your inbox:    krystenconner.com
--> Schedule a consult here:   https://scheduler.zoom.us/krysten_conner/coaching-consult

I help AEs win 6-7 figure deals to overachieve quota & maximize their income

pclub.io

Multi-thread Your Way to 34% Higher Win Rates 
Access multiple Decision Makers faster with proven templates & approaches
Expand your footprint and get "high and wide" access to multiple influencers in your top deals.

Sign up for the Multi-threading Masterclass here!

Course Author:  Multi-Threading Masterclass

Outbound Squad

Helping you pack your pipeline with qualified meetings.  Especially those shiny new logos.

Coach

Outreach

• 10-27% more revenue (Forrester study)
• 31% more meetings booked
• 29% more opportunities

Outreach is like Amazon for sales activities.  Makes everything about it faster & easier, more trackable, and you get better info for better decisions.  Frees you from mundane work. So you can do revenue generating work.

But don't take our word for it.  Adobe, Tableau, Zoom and 5,000+ other clients get extraordinary results with Outreach's system of action. Salesforce, Microsoft and SAP have all invested millions in Outreach.

Honeywell, Cisco and SAP drive predictable and measurable growth, increase efficiency + effectiveness of all customer-facing teams, and improve visibility into sales activity and performance with Outreach.

Enterprise+ Account Executive

Outreach:
• Forbes Cloud 100 for 2018-2020
• #1 in G2's Best Products for Sales, 2020
• $4.4B valued "Unicorn" 

Hustle + grit, being a decent human, and helping clients get what they needed were my 'few & vital'
 
Led to these results:
• #1 on my team and #3 in all of Enterprise for New Logo acquisition
• 711.21% YoY ARR growth in my book - all New Logo
• Top 3 rep in East region for new ARR, with 47.6% win rate 

Outreach optimizes every touch throughout the customer journey, managing interactions across email, voice and social.  Machine learning guides sales and service teams to take the next right actions.

Headquartered in Seattle but with offices in San Francisco, Tampa, and London, Outreach has received $289M+ in funding from top tier investors. **Backed by Salesforce & Microsoft** as well as Lone Pine, Meritech, Spark, DFJ Growth, Sapphire, Trinity, Floodgate, Mayfield, Premji Invest, Steadfast Capital Ventures, Sequoia Capital, Tiger Global Management Vista Equity Partners, Microsoft, SAP and Salesforce Ventures

Enterprise Account Executive

Tableau Software

How do you actually accomplish digital transformation, in real life? How have others built a data culture? What have they gained as a result of all that time and effort?

Working with clients to answer these questions helped me achieve: 
• 137.73% YoY growth in my book - this put me in the Top 7%; #5 out of 63 reps
• 145.36% of Services quota; #22 out of 63
•  41% partner attachment (sales is a Team Sport)
• The honor of presenting to my peers on Prospecting at GSKO 2020

Enterprise Accounts, Financial Services

PowerSchool

PowerSchool creates tech that makes it easier, faster, and more cost-effective for schools to find and
keep great teachers. As a former teacher, this was a purpose close to my heart.

In this role, I worked with large school districts and associations (5,000 - 50,000 employees) across
5 states. This included all stages of the sales cycle: market development, new business sales and
expansions.

• Truly partnering with the districts I served allowed me to achieve an average of 127% of my revenue goals every quarter.  
• This partnership approach also helped me do 14X what prior reps had done in the same geographic territory.
• Over 61% of my clients had never worked with us before.  Earning their trust was an honor.

Strategic Accounts

Hello Alice

Super pumped about getting my side hustle accepted into this national accelerator.  Circular Board was the Start-Up Accelerator that launched Hello Alice.

Founder - Member of Fall 2016 Founders Cohort

Haas & Wilkerson Insurance

Haas & Wilkerson is one of the nation's largest privately held insurance brokers.  I worked as a Risk Consultant partner for high attendance entertainment events across the country. 

• Created Challenger Sale strategy for National Accounts division (slide deck below)
• Sales and Business development for National Accounts division, both for-profit and nonprofit
• Strategic Sales Partnerships project team

Strategic Account Executive (Field)

My clients were all small/medium businesses and nonprofits, run by folks driven to pursue their dreams, passions and callings.  It was a thrill to develop creative solutions for their organizations.  

While the numbers alone can never tell the whole story, they do help quantify impact:
• Sales, new business development and client retention, as well as growth and operations strategies for our agency’s fastest growing unit (growth rate of 21% during my tenure)
• Created improved work processes that cleared 5 months of backlog within 8 weeks
• Introduced pilot program that increased efficiency of analysis process by 48%

Business Unit Manager - Select Accounts

🚫pipeline anxiety l Terrible dancer l Always a Teacher 🦄🦄🦄 ex Outreach, Salesforce, Tableau 👉🏼👉🏿👉🏽 Click bell/top right to be notified when I post 🔔

Feel like you're trying to do everything right… but deals keep slipping, ghosting, or dragging out forever?
You’re not alone.

Enterprise sales is full of hidden traps no one warns you about:
 ❌ Deals that seem real but never close
 ❌ Discovery calls that stay surface-level
 ❌ No clear way to qualify quickly—or confidently
 ❌ “Great calls” that vanish into silence
 ❌ A cycle that feels out of your control

And somehow, you’re still expected to hit an aggressive number.
In a tough market. With no real playbook.

It’s exhausting—and it’s not your fault.


The worst part? You don’t feel in control.
You’re anxious. Burnt out.
And starting to wonder if you're even cut out for this.

But it’s not you.
You were just never taught how Enterprise sales actually works.


What if you didn’t have to figure it out the hard way?


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I hit 47.6% win rates, broke records, and 14X’d territory expectations—but it didn’t start that way.

Early in my career, I felt stuck and scattered too. I had to teach myself how to run deals with structure, control, and confidence—because no one else was doing that kind of coaching.


Now, I teach you the strategies I wish I had sooner:
 ✅ Run Discovery that actually drives urgency
 ✅ Qualify fast—without sounding like a jerk
 ✅ Multi-thread without being annoying
 ✅ Speak the language of Executives
 ✅ Lead deals so buyers want to follow


Here’s what clients say after working together:
 👉 “Went from 2% of my number to 106%”
 👉 “Helped me close a deal with a $5B account - that 2 of my predecessors failed to close.”
 👉 “I closed the largest contract in my company’s history from prospecting to close because I implemented in real time what she taught me.“


You don’t need another sales theory.
You need someone who’s been in your shoes—and knows how to win big deals now.


Want to sell like a top performer—without waiting 10 years to figure it out?
Let’s work together: krystenconner.com


🟢 I offer 1:1 coaching for individual reps, and workshops for sales teams who want to win bigger, faster, and more often.


Browse client wins here: https://www.linkedin.com/in/krystenconner/details/recommendations/



💫"We pay for every lesson with either time or money. And we use the currency we value least."
         -Alex Hormozi

Member

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

Mike Gallardo

Cold call tip: When you get an objection say "actually, that's why I called" 🤯


Here's how it works:


𝟭. 𝗦𝗲𝗻𝗱 𝗺𝗲 𝗮𝗻 𝗲𝗺𝗮𝗶𝗹.

Actually, that’s why I called.

Figured sending an email would create more questions than answers. And thought you may be curious how similar [persona] are achieving [positive business outcome].


𝟮. 𝗪𝗲’𝗿𝗲 𝗮𝗹𝗿𝗲𝗮𝗱𝘆 𝘂𝘀𝗶𝗻𝗴 [𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗼𝗿].

Actually, that’s why I called.

[similar company] was using [competitor] and liked that we could [differentiator]. 


𝟯. 𝗪𝗲 𝗱𝗼𝗻’𝘁 𝗵𝗮𝘃𝗲 𝗯𝘂𝗱𝗴𝗲𝘁.

Actually, that’s why I called.

Figured you wouldn’t have a budget right now, but hoped to share how we’re helping [similar persona] achieve [positive business outcome] so when you’re ready you know what’s out there. 


𝟰. 𝗜’𝗺 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗽𝗲𝗿𝘀𝗼𝗻.

Actually, that’s why I called.

I’ve researched your company and I’m not sure to talk about [positive business outcome]. Figured you’d benefit from this. Any recommendation on who to reach out to?


𝟱. 𝗪𝗲’𝗿𝗲 𝗮𝗹𝗹 𝘀𝗲𝘁.

Actually, that’s why I called.

Figured you’d have something in place. [similar company] said the same but liked that we could [differentiator].


𝟲. 𝗜’𝗺 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗺𝗮𝗸𝗲𝗿.

Actually, that’s why I called.

I thought there would be a few people involved in the conversation, but was curious if [positive business outcome] would help you personally.


Shoutout to Jeb Blount for this strategy. Give him a follow if you're not already!


What's your go to for objections?

- Mike G

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

The best AEs ask killer discovery questions.

Here's my top 10:


Notice:
They're all focused on priorities and challenges.
(That's not a coincidence!)

𝗧𝗵𝗲 𝗕𝗲𝘀𝘁 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀:

1. "You mentioned X. Would you say that's the most important thing you're looking to accomplish with a solution like ours?" Always seek to understand their number one priority.

2. "Appreciate you sharing, Jill. Sounds like X is a priority. Curious if you could share more about that?" Have a real conversation (ie actively listen) and ask follow up questions. Don't just use a checklist for discovery.

3. "Thank you for running me through everything, Jill. I work with a lot of clients in your situation. Usually, X and Y are the biggest priority for them. Is that the same for you?" Leverage your experience and subject matter expertise to give options.

4. "When you say X is a challenge, what do you mean by that exactly?" Never take an initial challenge shared at face value. Dive deeper always.

5. "One thing I'd like to understand is what's most important to you. Would you mind walking me through your evaluation criteria? Are there 1 or 2 things that really stand out as the most important for you and your team?"

6. "When it comes to [process] who else on your team is involved? And have they mentioned anything being a challenge around that?" Don't just ask questions about your prospect learn about their team too.

7. "For your [other decision maker] what would you say is the biggest priority for them in this evaluation?" Great question for uncovering priorities/challenges of key stakeholders.

𝗠𝘆 𝗕𝗶𝗴𝗴𝗲𝘀𝘁 𝗧𝗶𝗽𝘀:

1. Write down your favorite questions when it comes to discovery and uncovering the challenges and priorities of your prospect.

2. For each product you sell write down the most common challenges you solve and the questions you ask to see if your prospect is experience them too.

3. Review your discovery calls and give yourself an honest assessment on how well you uncover the priorities and challenges of your prospect.

4. Have your manager review a call specifically for uncovering challenges and priorities on a discovery call.


What's your biggest tip when it comes to discovery?

- Mike

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

My best outbound sequence structure. 
 
Here's the breakdown:
- 4 Emails 
- 6 Cold Calls 
- 3 LinkedIn Messages 
 
All sent over a couple weeks.

Feel free to adjust it so it works for you and your style.
 
♻️ And then try again 30 to 90 days later with new messaging. 

 
𝗠𝗼𝘀𝘁 𝗜𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁𝗹𝘆: 
 
This is all you need, I promise.
 
Gone are the days of 20+ touches over 20+ days [including break up emails]. 

Keep it simple.
Keep it valuable.
And try again later if it doesn't work.

Your SQOs and email domain health will thank you.
 
 
What would you change? 
 
- Mike G 
 
 
👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7

li_at

JSESSIONID

Talks about #sales, #startups, and #leadership

Sales Director at Deel

She always hits 150% more of quota.

Here's how:

She asks the hard questions:

1. "I know you and I are aligned, but for this to actually get signed, what's the most common reason deals like this usually get paused or killed internally at your company?" Gets your champion to share potential hurdles or internal challenges that you can partner on solving and/or getting ahead of.

1. "Let's say everything goes perfectly on our side. Is there anything on your side that could possibly prevent us from moving forward?" Uncovers internal risk factors and political landmines you can help them navigate.

2. "When was the last time your team successfully implemented a new system or vendor like this? What were the key lessons learned from that process?" Great question to learn their history with change and potential internal inertia or pain points related to adoption that they've experienced before.

3. "Out of all the priorities you're juggling right now, where does solving this particular problem rank? Is it a 'must-solve-now' or a more 'nice to have eventually?" Dives into the genuine urgency and whether the problem is painful enough for immediate action.

4. “You mentioned [X date] as a goal. What’s driving that timeline, and is that date firm?” Verifies whether the timeline is real or aspirational.

5. "Based on what you’ve seen so far, is there anything that’s giving you pause about moving forward with us?” Invites honest feedback to surface objections early.

6. “How does our solution compare to others you’re evaluating?” Tests competitive positioning and whether you're the frontrunner.

7.“Who else on your team needs to feel good about this before a decision is made?” Pushes beyond your main contact to build a map of the buying committee.

8. “If [insert key stakeholder] were here, what concerns would they raise?” Forces your champion to think on behalf of other decision-makers.

9. “Have you ever purchased something like this before? What did that process look like internally?” Surfaces potential red tape or hidden decision criteria.

10. “What needs to happen between now and [target close date] for this to actually happen?” Pushes them to co-create the buying journey and surface risk.


What's your favorite hard question to ask?
- Mike G

👉 Black Friday Special: Get $53 off The Best Sales Course (this week only!) https://lnkd.in/gEkPHuZ7

One of my best AEs crushes quota.

Steal her demo questions.

 
 
𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝘀𝗵𝗲 𝗱𝗼𝗲𝘀𝗻'𝘁 𝗮𝘀𝗸: 
 
1. Does that make sense? 
2. Any questions? 
 
 
𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝘀𝗵𝗲 𝗮𝘀𝗸𝘀: 

1. "Last time we spoke you mentioned [context]... Has anything changed since we last spoke?" Great way to confirm priorities, challenges and see if anything's changed.

2. I listened back to our last conversation and noticed [context]... one thing I forgot to ask about was [question]?" Great way to dig into priorities, challenges or key areas you want to learn more about.
 
3. "What was running through your mind as I was sharing that?" Great question to ask after showing an important feature. 
 
4. "Before I show you how to X can you walk me through your process step-by-step?" Great question to ask before showing a key feature so you can really compare and contrast. 
 
5. "When you need to X what happens?" Great process question for learning their step-by-step process for key workflows. 
 
6. "Who else on your team would benefit from being able to X?" Ask this to multithread. Ideally, you do some research ahead of time and can drop some names in there. 

7. "I noticed we have about 8 minutes left in our call today. If it's alright with you I'd like to chat through pricing and next steps. Does that work?" Always watch the clock and save enough time to discuss/recommend what happens next.
 
 
Bonus tip: Stop your screen share when asking these questions and have a face to face conversation. 
 
- Mike G 
 
 
👉 Black Friday Special: Get $53 off The Best Sales Course (this week only!) https://lnkd.in/gEkPHuZ7

My best AEs run killer demos. 

Steal all their best moves:


𝟭. 𝗪𝗵𝗮𝘁 𝘄𝗲 𝗵𝗲𝗮𝗿𝗱 𝘀𝗹𝗶𝗱𝗲. 
Start the call with one clean slide showing what you learned from your discovery call. Focus the content on priorities and challenges. Ask them to confirm everything is accurate.

𝟮. 𝗔𝘀𝗸 𝗱𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀. 
Discovery doesn't stop after the first call. If anything, discovery is more important on the demo. My best AEs prepare the questions they want to ask ahead of time.

𝟯. 𝗢𝘂𝘁𝗰𝗼𝗺𝗲𝘀 𝗼𝘃𝗲𝗿 𝗳𝗲𝗮𝘁𝘂𝗿𝗲𝘀. 
Everything they show is focused on how they will help with the priorities and challenges that they learned about on the first call. They don't just show something to show something.

𝟰. 𝗦𝗲𝘁 𝗻𝗲𝘅𝘁 𝘀𝘁𝗲𝗽𝘀. 
After the second call you should know if this is a good fit or not. Assuming it is means you should feel confident talking about what the process from here will look like. Take the time to map it out.

𝟱. 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁𝗶𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝘀𝗼𝗹𝘂𝘁𝗶𝗼𝗻. 
No matter what you show there should be talk tracks around why it's better, more effective, more valuable compared to other products in the market. 

𝟲. 𝗠𝗮𝗻𝗮𝗴𝗲𝗿 𝗶𝗻𝘃𝗼𝗹𝘃𝗲𝗺𝗲𝗻𝘁. 
For larger deals including your manager on the call is a secret weapon. Most sales team wait until negotiation to bring in higher level folks. 

𝟳. 𝗔𝘃𝗼𝗶𝗱 "𝗱𝗼𝗲𝘀 𝘁𝗵𝗮𝘁 𝗺𝗮𝗸𝗲 𝘀𝗲𝗻𝘀𝗲?" 𝗼𝗿 "𝗵𝗮𝘃𝗲 𝗮𝗻𝘆 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀?". 
Ok to ask these every now and then but generally speaking you should have some questions you ask instead of these to make the most out of the conversation.


What did I miss?

- Mike G

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

3 hot takes that I believe in:

1. All remote > than in office and hybrid
2. Almond milk > oat milk
3. Demo on the first call


𝗣𝗼𝗶𝗻𝘁 𝟭.
Nobody can afford to live in big cities anymore. A lot of great talent is in the middle of the country. Commuting is the worst.

𝗣𝗼𝗶𝗻𝘁 𝟮.
Health reasons only. Oat milk is loaded w/ sugar. I'm sorry to break the news to you. Please forgive me.

𝗣𝗼𝗶𝗻𝘁 𝟯.
Learn their priorities and challenges. Demo one thing that can help with that. Build interest for scheduling a longer more in depth demo.


What's your hottest take?

- Mike G

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

I'm hiring AEs! 🥳

Here's why you should apply today:

𝟭.𝗤𝘂𝗼𝘁𝗮 𝗔𝘁𝘁𝗮𝗶𝗻𝗺𝗲𝗻𝘁
Our North Star is over half the team hitting quota every month. Most months we outperform that. Last month over 70% of the team exceeded quota and our top performers consistently run at 200% or more. Huge earning potential here.

𝟮. 𝗟𝗲𝗮𝗿𝗻𝗶𝗻𝗴 𝗮𝗻𝗱 𝗚𝗿𝗼𝘄𝘁𝗵
You will work closely with high performing AEs who truly want each other to win. The bar is high at Deel and the team is open, collaborative, and supportive when it comes to sales strategy, deal execution, and leveling up fast.

𝟯. 𝗠𝘂𝘀𝘁 𝗛𝗮𝘃𝗲 𝗣𝗿𝗼𝗱𝘂𝗰𝘁
Deel is the clear product leader in this space. It is not close. You get to sell a full suite of solutions and you'll definitely get deals that feel more like mid market than SMB because of the complexity and size.

𝟰. 𝗟𝗼𝘁𝘀 𝗼𝗳 𝗜𝗻𝗯𝗼𝘂𝗻𝗱 𝗟𝗲𝗮𝗱𝘀
Inbound makes up the majority of your pipeline. You will still outbound your own opportunities, but you will have a strong flow of warm leads to build and scale pipeline quickly.

𝟱. 𝗧𝗼𝗻𝘀 𝗼𝗳 𝗣𝗿𝗼𝗺𝗼𝘁𝗶𝗼𝗻𝘀
We run promotions every 3 months. I'm approaching 100 promotions at Deel in under 5 years. We have seen AEs move into mid market, enterprise, SDR leadership, and sales leadership. Real career acceleration exists here.

𝟲. 𝗔𝗹𝗹 𝗥𝗲𝗺𝗼𝘁𝗲
Deel is remote forever and always. For this role you must be based in the United States or Canada. Work from anywhere while selling globally.

𝟳. 𝗪𝗼𝗿𝗹𝗱 𝗖𝗹𝗮𝘀𝘀 𝗠𝗮𝗻𝗮𝗴𝗲𝗿𝘀
Our managers go above and beyond to support their AEs. They are deeply invested in your growth, your performance, and your long term career. You will not find better sales leaders to learn from.

Interested?
Apply here: https://lnkd.in/gB2xPVNy

Questions? 
Let me know in the comments!

- Mike G

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

Every cold call opener you could ever need.

All in one place for you.

1. "Hey [name], This is [name] with [company], I know you didn’t expect me to call you this afternoon, do you mind if I take one minute to tell you why I called you specifically, and then you can tell me whether or not it makes sense to speak?"

2.“Hey [name], this is [name] from [company]. I know you’re not expecting this call, so I’ll keep it very brief.”

3. "Hey [name] - I noticed [context]. This is a cold call but it's a well researched one. Have a moment? I promise to be brief."

4. "Hey [name] - You might hate me because this is a cold call. But it's a well researched one about [context]. Have a quick moment to hear why I called you specifically?"

5. "Hey [name], this is [name] from [company]. I know you weren't expecting my call. Do you have a moment? I promise to be brief."
 
6. "Hey [name] - This is a cold call but it's a well researched cold call. Can I have 30 seconds to tell you why I specifically called you?"
 
7. "Hey [name], this is [name] with [company]. Good morning. I’m reaching out about X. Do you have a quick moment?" 
 
8. "Hey [name] - This is [name] with [company]. I know I probably caught you in the middle of something. Do you have minute for me to tell you why I’m calling and you can let me know if you’d like to keep chatting?" 
 
9. "Hey [name] - This is [name] with [company], I know you didn’t expect me to call you this afternoon. Do you mind if I take one minute to tell you why I called you specifically, and then you can tell me whether or not it makes sense to speak?" 
 
10. "Hey [name], this is [name] with [company]. I know you weren’t expecting my call. Do you have a minute for me to explain why I’m reaching out, and you can decide if it’s worth continuing the conversation?” 
 
11. "Hey [name], this is [name] from [company]. I’m calling to see if you’re open to discussing how we can help you X. Do you have a quick moment?" 
 
12. "Hey [name], [name] here from [company]. I’m reaching out about X. Is now a good time to have a brief chat?"
 
13. "Hey [name], [name] with [company] here. I noticed you’re [insight] and might be interested in X. Do you have a moment to discuss?" 
 
14. "Hey [name], this is [name] from [company]. I’m calling because we’ve helped companies like yours [value prop]. Can we chat for a couple of minutes?" 
 
15. "Hey [name], [name] here with [company]. I understand your time is valuable, but do you have a minute to hear how we’ve [value prop]?" 

16. "Hey Jill - It's Mike at Acme. Was hoping to make your day with a cold call this Friday. Have a moment to hear why I specifically called you?" 

17. "Hey Jill - You're gonna hate me but this is a cold call. Do you have a sec so I can tell you why I called?" 
 

Which one's your favorite?

- Mike G

👉 Black Friday Special: Get $53 off The Best Sales Course (this week only!) https://lnkd.in/gEkPHuZ7

He closed a $1,000,000 deal at Deel 🥳

I listened to every single call.

Here's how he did it:

1. He built the plan with the buyer.

He created a clear roadmap. It detailed every milestone and required action for both sides. “I’ve put together a proposed mutual commitment plan for us. I'd love for us to spend the first 15 minutes aligning on this together...”

2. He obsessed over decision criteria. 

He knew precisely what mattered to the buying committee. Every feature discussion was framed as a path to a key business result. “Let’s talk about the final evaluation. What criteria will be most important to your team? What does a 'win' look like for the internal stakeholders?”

3. Each call had a clear objective

Instead of assuming, he checked in to ensure the meeting's purpose was aligned with the buyer’s current needs. This built trust and made sure he was focused on the right things. “Here's my objective for this call... [objective]. Is there anything you'd like to add?”

4. He preemptively addressed roadblocks

He brought up common implementation or organizational hurdles before the client could. He then shared proof of how they were successfully mitigated by others. “In other global expansion deals, we often see [mention common hurdle]. Is that a potential wrinkle you’re anticipating here, or is there anything else we should make sure to think through?”

5. He leveraged Internal expertise. 

He knew when to step back and let a specialist take the lead. Key stakeholders were introduced based on their specialized knowledge. “Knowing this is a complex integration, I've asked [name], our [role], to join. They’ll walk you through X, and will be a great internal resource you can leverage at Deel moving forward.”

6. He maintained a disciplined structure

Every meeting was tightly managed and executed with professional precision. He never let the time or agenda run away. He always began with: “For our time today, I propose a quick 5-minute review of last steps, a deeper dive on the integration process, and then we'll save the last 10 minutes to schedule our next official check in. Does that sound good?”

7. He used "before & after" narratives. 

He didn't just rattle off case studies. He told compelling stories focused on transformation, framing the client's past pain against their future success. "Take the example of a [client name]. Before working with us, they were struggling with [pain point] every quarter. Now, after implementing our solution, they've been able to [action] leading to an overall improvement in [details]."


What tip would add for your biggest deals?

- Mike G

👉 Black Friday Special: Get $53 off The Best Sales Course (this week only!) https://lnkd.in/gEkPHuZ7

How to go from SDR to AE.

In 4 simple steps:


𝟭. 𝗣𝗶𝗰𝗸 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗰𝗼𝗺𝗽𝗮𝗻𝘆
If you're not working somewhere that does a lot of SDR to AE promotions it's going to be hard to make the jump. I've been at places where 15 SDRs are applying for 1 AE role once a year. At Deel I will promote 20+ SDRs to AEs this year. Big difference.


𝟮. 𝗢𝘂𝘁𝘄𝗼𝗿𝗸 𝗲𝘃𝗲𝗿𝘆𝗼𝗻𝗲 𝗲𝗹𝘀𝗲
Hustle and tenacity is the 80/20 of succeeding in sales. This applies to SDRs, AEs and Managers alike. Everyone is different obviously but hard to be a top performer if your schedule is not on point and you're consistently operating at a high level. 


𝟯. 𝗕𝗲 𝗮 𝘁𝗼𝗽 𝗽𝗲𝗿𝗳𝗼𝗿𝗺𝗲𝗿
If I had to pick one habit that drives top performance it's getting and applying feedback. Seek out how you can be better proactively with your manager. Be self aware. Study top performers.


𝟰. 𝗟𝗲𝗮𝗿𝗻 𝗔𝗘 𝗳𝘂𝗻𝗱𝗮𝗺𝗲𝗻𝘁𝗮𝗹𝘀
Don't wait for the interview process to learn what it takes to be a successful AE. Take the time to study the fundamentals and use every resource (like your AE buddy) at your disposal.


𝟱. 𝗕𝘂𝗶𝗹𝗱 𝘆𝗼𝘂𝗿 𝗶𝗻𝘁𝗲𝗿𝗻𝗮𝗹 𝗯𝗿𝗮𝗻𝗱
Once you're a top performer share your knowledge with the greater team. Shoot no ask messages that are valuable to Sales Managers and Sales Leaders. Don't assume people know who you are. Go out there and build the narrative yourself. Take full responsibility of this.


What would you add?

- Mike G

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

He closed a $650k deal. 🤯

One of the biggest I've ever seen in SMB.


He’s a rockstar.

And here's how he won it.

Hint: It all came down to post demo effort.


What he did post demo:

1. Recapped progress constantly
He kept everyone aligned at every stage. Summarized what they cared about, how we solved it, and why we’re different. Especially when new stakeholders got involved.

2. Pulled in leadership early
He didn’t wait for a late stage “exec introduction.” He added his manager to calls immediately, strategized pricing with her, and had her message their team. Which built a ton of trust and confidence. Especially since our competitors didn't do this.

3. Tailored everything to their business case
He created custom resources based on their priorities. The decks weren’t generic. They were written in the customer’s language, mapped to their goals, their metrics, their outcomes. They felt heard.

4. Ruthlessly prioritized the account
He treated this deal like his only deal. Moved meetings if needed. Took calls outside of standard hours. If the customer needed him at 7am or 8pm, he was there.

5. Lightning fast response times
Emails didn’t sit. If something came in after hours, he responded quickly anyway. Labeled their emails so they surfaced to the top of his inbox. Nothing more important than responsiveness imo.

6. Organized everything in one shared space
Any piece of content that will help the deal move forward (slides, timeline, differentiators, call recordings, etc) live in his Aligned room. He monitors where stakeholders are spending time and is proactive with his communications. Which leads to…

7. Created a shared Slack channel
Connected their team with ours: onboarding, specialists, leadership. Between his digital sales room and slack channel he eliminated long email chains. No bottlenecks. Problems got solved fast.

👉 Get the template here: https://lnkd.in/g3GfNi7m


8. Stayed close during onboarding
He didn’t “throw it over the fence.” Stayed involved so the customer never felt handed off. Buyers love when their AE sticks with them through go live.

9. Validated priorities constantly
Instead of assuming anything, he kept checking in: “Is this still the most important thing?” “Did anything change internally?” No guessing. No surprises.

10. Used customer proof instead of feature pitching
Short, relevant before/after stories about customers he personally helped. He built trust immediately with real world stories and references.


Who says you can’t close massive deals in SMB?

– Mike G

Last July I promoted 4 SDRs to AEs.

And now they're all the top AEs on the team.

Literally no better feeling than that :)

- Mike G

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

Step 1: Get into sales.
Step 2: Work super hard.
Step 3: Make a bunch of money.
Step 4: Invest as much as you can.

- Mike G

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

I took a 60% pay cut joining Zenefits.
I took a 10% pay cut joining Flexport.
I took a 6% pay cut joining Deel.

I know this seems crazy.

But it's not really

1. Making 10 Year Moves. 

I was focused on the long game. Every decision was measured against the next decade, making me comfortable with smaller, short term setbacks if they pointed toward massive future growth.

2. The New Financial Reality. 

Inflation and the cost of living are insane and it's dramatically harder for our generation than it was for earlier ones. You need to target a much higher income (and invest wisely) just to get ahead.

3. Joining a Rocket Ship. 

Joining a company during its rapid growth phase provides a ton of opportunity. If the business is scaling fast and you perform well, the promotions, raises, and opportunities practically create themselves.

4. Optimizing for Skill Acquisition. 

My priority wasn't just the paycheck; it was about becoming the strongest sales leader I could. I value maximizing learning about new business industries, business models, and new challenges.

5. Genuine Product & Market Fit. 

I genuinely believed in the mission. Being passionate about the problem the product solved, the company's competitive edge, and the customers we served.

6. Building an Equity Portfolio. 

Having options across multiple companies hedges risk. Joining early means you receive significantly more generous grants, and you only need one successful IPO to dramatically change your financial trajectory.

7. All Remote = Freedom. 

For me, being fully remote was non negotiable. That flexibility was key to getting a house and avoiding the crippling expense of living in tech hubs like San Francisco or New York.

8. Choosing Your Leadership.

I paid close attention to who I'd be reporting to and who was leading the company. You rise faster when your managers are genuinely invested in your career progression and success.


𝗠𝘆 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆: Don't be afraid to bet big on yourself, take risk and make moves. Turned 40 recently and have really learned that life's too short to play small. 

- Mike G


👉 Black Friday Special: Get $53 off The Best Sales Course (this week only!) https://lnkd.in/gEkPHuZ7

I'm doing so many internal interviews right now.

SDRs to AEs
SMB AEs to MM AEs
AEs to Manager

Nothing gets me more fired up!

- Mike G

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

My best AEs make more money than me.

And that's how it should be.

- Mike G

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

We do promotions every 3 months.

I've never seen that at any other startup.

Here's the thing.

If you're looking to sell somewhere with:

1. A high performance culture
1. Where your results are rewarded
2. And there's a ton of career opportunities

There's literally no better place than Deel.

- Mike G

👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7

The best time to work on yourself, your game, and everything you're doing in sales is when you're winning.

That's when it becomes easy to:

1. Let good habits slip
2. Fall back into bad habits
3. Not work or try as hard as you were
4. Get complacent and stop improving yourself 
5. Hit a serious plateau and not realize it until too late


When you're failing or not doing well.
It's obvious that you need to change things.

But the biggest mistakes and step backs (that I see) often happen when people are too comfortable or on a winning streak.

Getting to the top of the leaderboard is one thing, but staying there consistently over time is a completely different beast.


- Mike G

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

How to book meetings after a prospect has ghosted you.

We've all been there:

1. Calls go great
2. You uncover pain
3. Everything going to plan
4. And then out of nowhere... crickets


Happens to the best of us.

And for a lot of different reasons.

Oftentimes, for things outside your control.


But have no fear. These scenarios are actually pretty easy to save. Just requires being persistent and sending valuable emails like the one below.


𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝘁𝗲𝗺𝗽𝗹𝗮𝘁𝗲:

Hey Jill,

Last time we spoke you mentioned you’re considering doing SKO in March 2025.

Have this [report/doc/video] on X that walks through everything you need to know: [insert short link].

Which countries to choose, the best events to have and how to structure the trainings.

Thought you’d find it helpful.


What's your best tip for getting meetings back on the books?

- Mike G

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

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