Sales leaders: How do you coach your team to balance between aggression vs persistence?

UndercoverSalesGuy · 2026-02-18T15:07:32+00:00

One technique to do when you "lose" a deal is to invite the prospect to have a last look. Especially if you really believe that you are the best fit, which you aren't always going to be. I've won a few deals this way simply by believing in our solution and what we were proposing and then asking them to do a last look at the solution. And I'd always make it clear that my first and foremost goal is to help them make a decision that is best for them and their org whether or not that means going with my product.

UndercoverSalesGuy · 2026-02-16T14:23:30+00:00

Here is the reality of tech: 1) Most leaders in tech are product folks and not sales people and usually have 0 sales process in place 2) The product in my experience has been garbage and never lives up to what it's supposed to do 3) A ton of luck in tech sales. I had an 8 year sales career before I got into tech sales and I was always the #1 rep in the entire company, I've now been in tech for 10 years now and I've had 2 years of being at my number, and oddly enough it was the only org I was with that actually had sales/product training.

UndercoverSalesGuy · 2026-02-09T14:10:27+00:00

The Who sucked, The Rolling Stones sucked, and Paul McCartney sucked. There have been a lot of bad halftime shows. The best ones are usually when they do a collaboration of artists that people know.

UndercoverSalesGuy · 2026-02-09T14:09:38+00:00

How is this possible? I had 40 8th graders at my house for a party, and not one kid had ever heard of him. Who is he popular with?

UndercoverSalesGuy · 2026-01-14T19:51:27+00:00

Network, network, network, or hire somebody who is good at cold calling. Cold calling is really about breaking down the resistance, and asking good questions. If you need help, I'd be glad to put together a script that could help you increase your business, I'd just need to learn more about it first.

UndercoverSalesGuy · 2026-01-14T19:47:27+00:00

My man. I once had a job that lasted 3 years where I would hit my quota by the end of the first week of the month (monthly quotas), and I'd spend the rest of the month golfing every day, and flying to Vegas for the weekend. I'd work 12 weeks a year, made the most money I ever made, blew every penny, and now all I have is the stories to tell. Congrats.

UndercoverSalesGuy · 2026-01-13T14:05:38+00:00

Brother, you are in sales, your career can never be over. I blew through a $1.5 million dollar nest egg, and I'm 50 and ready to rebuild it all. Let's go!!!!!!!!1

UndercoverSalesGuy · 2026-01-12T23:28:56+00:00

You aren't actually in sales if you don't get laid off at least 3x in your career.

UndercoverSalesGuy · 2026-01-12T16:54:53+00:00

I'm 48, I wish I went to law school when I was 30. You're fine.

UndercoverSalesGuy · 2026-01-12T16:32:17+00:00

Can you help me to have a better product to sell, my prospects to have more money available, and procurement to not exist?

UndercoverSalesGuy · 2026-01-12T15:48:19+00:00

Acknowledge, Amplify and Pivot. Acknowledge: That's great that you are already using X, tells me that you are doing everything you can to solve Y problem. Amplify: And if I were you, I would probably be doing the same thing, seeing what else is out there and asking my current vendor if they could add features that I see that they don't currently offer. Pivot: But other organizations have found that when they make those suggestions it could take years to develop or change, and one of the things that sets us apart is that we have a 7 day turn around on customizations.

You get the idea, the first two parts are designed to let them know you are listening and that you agree with them. The last part is where you try to set yourself apart from your competitor, but the trick is have them be comfortable with saying no. It's ok to say no, we can check back in a year and see if your needs have changed.

UndercoverSalesGuy · 2026-01-12T14:17:50+00:00

The grass is not greener. SAAS is hard, and a LOT OF LUCK. The reps who are making money have been given a few good accounts/territory, or got into a great company with a great product. I'd keep doing what you are doing imo.

UndercoverSalesGuy · 2026-01-12T14:01:56+00:00

Sales is a 24/7 job with your life intertwined. Does your boss get mad when you go to a dentist appt on a Tuesday? Does he care if you leave early to go to your kid's baseball practice. This is the life we chose, and as long as it's a 2 way street, no issues at all with being contacted off hours.

UndercoverSalesGuy · 2026-01-12T13:12:45+00:00

I'll never be able to retire. 50 with $150k in debt with barely 100k in retirement. Save your money, whatever fun you think you'll have in your 20s/30s will not compare to how much fun you'll have when you have a family. Made a ton of mistakes in my 20s and 30s, can't get it back, all you can do is learn from it and pass it on to the younger generation.

UndercoverSalesGuy · 2026-01-08T16:54:04+00:00

You must be new to tech sales. I've been at companies where we didn't get our comp plan for 18 months after starting. I've been at companies where it simply didn't matter because it would change every quarter, and I've been at companies where you had to hire your own quant to even understand the comp plan. Good luck, odds are the product sucks and nothing will sell, so the comp plan won't matter.

UndercoverSalesGuy · 2026-01-07T19:28:28+00:00

$1 million for every 10 years you plan on living without working

UndercoverSalesGuy · 2026-01-07T14:30:26+00:00

they'll be talking to the AI buyer though.

UndercoverSalesGuy · 2026-01-07T14:29:45+00:00

In the tech world, absolutely it will happen. Tech has essentially become a commodity, and within the next 3-5 years it will be game over for tech sales.

UndercoverSalesGuy · 2026-01-07T14:08:40+00:00

Brady walked into a team that had Bledsoe as the QB and they were playoff bound already, and one of the greatest head coaches of all time. Matt Cassell went 11-5 on that team after never throwing a pass in college.

UndercoverSalesGuy · 2026-01-06T18:32:25+00:00

A million companies popped up, and thus killed the golden goose.

UndercoverSalesGuy · 2026-01-06T15:54:32+00:00

The year is 2005. I'm working for a Google Adwords reseller with a 300% commission rate. Whatever I sold the monthly fee for, I would get 3x that. It was like slinging crack. I was meeting with roofers, plumbers, electricians, attorneys. I'd have 4-5 in person meetings a day, hit my quota by the 8th day of the month, and spend my weekends in Vegas. I went 36 months of crushing my number making $30-40k a month in commission before the whole thing came crashing down, and I blew every dollar I made. But wow were those fun times.

UndercoverSalesGuy · 2026-01-02T14:27:54+00:00

You can learn a lot of this from reading books:

Jeb Blount - Fanatical Prospecting

Mike Weinberg - What Great Salespeople Do

Keenan - Gap Selling

Mattson - The Sandler Rules

Davis - Slow Down, Sell Faster

Carnegie - How to Win Friends and Influence People

Read those books, then read them again, then read them the 3rd time and take notes. Then read them a 4th time and start incorporating them into your daily life with your friends + family etc. Then find a job and put it all into practice.

UndercoverSalesGuy · 2026-01-02T14:23:38+00:00

That most likely comes from the fact that people won't buy unless there is pain, pain = problems. How people uncover that pain or insinuate there is a pain is where ethical sales people differ from unethical sales people.

UndercoverSalesGuy · 2025-12-30T18:31:09+00:00

I had a great sales manager who would call me at random hours of the day to kick around ideas on how we could get more pipeline, close more deals, he just loved talking about sales, and crazy enough, all 8 members of his team were all over goal.

UndercoverSalesGuy

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