HappyGilmore

Account Executive - SMB

AMA: On the tee, Happy Gilmore

What's up fellow WR peeps! @Gasty has invited me to be part of this week's AMA, and I'm honored to do so. Unlike Happy Gilmore (for those who've seen the movie), this meeting won't take place on the 9th green at 9.

For those who don't know me, I've been part of the war room for about 2.5 years now. Currently an AE at a software company operating in the HR/Comms space, and have been there for less than a year. Company I'm at is a leader in the space for employee experience, but has been going through a lot of changes recently, which have a lot of the sales team on edge.

Been in SaaS for over 4 years now after starting my sales career in sports ticketing, making hundreds of cold calls a day in my first role right out of college.

Open to answer and chat through anything, but would love to cover what it's like to move cross-country for a job, transitioning into a new industry and career, and navigating being part of a RIF.

Cheers my fellow savages,

Happy

29

30 comments

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oldcloser

Arsonist

8

💀

Do you think anyone has a chance of becoming a top producing seller without first starting off as a heavy dialer? Can you talk through the human hardening that happens as a result of hardcore phone life?

HappyGilmore

Politicker

5

Account Executive - SMB

I think it's a very slim chance. Starting off and doing heavy dials/prospecting, you go through the human hardening pretty quickly and it gives an answer as to whether a) I can do this or b) I'm not cut out for this.
It can take some time but as a result of the hardcore phone life, I just view rejection as part of the process and even welcome it. My thought is the worst answer I can get from a prospect, is no answer. If I at least hear that rejection on the phone or now in a deal, I can at least have an answer on whether we should meet.
For any new seller in a high call volume role, the faster they can not take the rejection personally, the faster they'll grow in their career.

Revenue_Rambo

Politicker

8

Director, Revenue Enablement

We’ve all got war stories. Would love to hear about your biggest crash and burn story, and how it changed your outlook on sales.

HappyGilmore

Politicker

4

Account Executive - SMB

This won't be deal specific, but actually job specific.
The last org I was at towards probably the last 6-9 months I was there, I had a totally shit attitude quite frankly towards the role, my performance, and where the company was going. To put it bluntly, I was blocking my own career progression.
Fast forward to November of last year, I was part of a reduction in force that took place at that company. Wasn't performance related, but think my general attitude I had at the time played a massive factor. After that I had to just go through my own emotions for the first couple of weeks and really digest what led to this point.
How it changed my outlook on sales, I view where I'm at right now as an opportunity and fresh start on my own career path in a way, and trying to be the best AE and teammate I can be each day, knowing that at any given moment, that bi-weekly paycheck can be gone in a flash. A lot more gratitude for how I view sales now versus a year and a half ago.

Revenue_Rambo

Politicker

3

Director, Revenue Enablement

This is such a great answer and reminder. So many of us are experiencing that right now. Ultimately you have the choice to be negative and bitch about everything that's going wrong, or do the opposite and be positive and focus your energy on how to make the things around you better.

HappyGilmore

Politicker

3

Account Executive - SMB

Totally. The big thing for me on this too was to just focus on what I can control. I can't control for example, what sales leadership implements that affects my role, or what sales ops is doing that affects me. I can only control my efforts with my role, and whatever outcomes take place from that, I can live with.

Sunbunny31

Arsonist

7

Sr Sales Executive 🐰

I’ll bite! I’d love to hear what it’s like to move cross-country for a job. That’s nothing I’ve ever done, so I’m intrigued by what led to the decision, how it affected your career path, and in hindsight, if you’d do it again.

oldcloser

Arsonist

7

💀

Dammit Bunny- I was gonna… OK, @HappyGilmore consider this double interest. Not gonna cop out though. Got another one.

HappyGilmore

Politicker

4

Account Executive - SMB

Moving across the country was probably one of the biggest risks I've taken in my life up to this point. 10 days after graduation, I packed the car and moved west to the Bay Area.
What led to that decision was for me, going after an opportunity to help build something new for a sports organization that really hadn't had a large sales structure before, and on top of that, wanting to have the experience of living somewhere new and if I didn't work out, I figured I could always move closer to home if need be.
It affected my career path in a way I didn't really expect to be honest. I was set on having a career in sports, but made the pivot a few years in (for a few reasons), and went into SaaS and was lucky to be in the right location for that industry when I did switch.
Looking back in hindsight I'd 100% do it again. That decision really shaped both my personal and professional life in ways I couldn't predict a year ago, and would go through some of the struggles of being far away from home again.

Sunbunny31

Arsonist

4

Sr Sales Executive 🐰

Good for you. How far did you have to come? I'm curious about your home base (midwest, south, etc), because the Bay Area is definitely different. Also, since you're in sports ticketing, I suspect you're working with one of the teams I follow. :)

HappyGilmore

Politicker

4

Account Executive - SMB

I came all the way from Ohio in the midwest, was a total change of scenery moving from there to the Bay Area.
While not in sports ticketing anymore (slinging SaaS), I did work for the Sharks as my first job out of college, and up at Cal for about 2.5 years. Had my best boss to this day still at Cal.

Sunbunny31

Arsonist

4

Sr Sales Executive 🐰

Sigh, Sharks. This has been a gruesome couple of years. Cal! I can see the Campanile from the top of the hill I live on.
Thank you for your story. Yes, CA is very different than OH. That's a big change!

Filth

Tycoon

1

Live Filthy or Die Clean

OHIO REPRESENT!

HVACexpert

Politicker

6

sales engineer

How did you get into sports ticketing? Seems like an interesting place to start a career.

HappyGilmore

Politicker

4

Account Executive - SMB

I was a sports management major coming out of college and went to a place that was really well known for that field and helping people break into that category and field choice. I did some different internships with other parts of the sports industry, and sales was the one area I gravitated towards.
It's a really competitive field and while there's less demand than when I entered the industry, that demand is still there.
That said, for as competitive of a field as it is to break in, it is an absolute grind of a career to be in whether you're just starting out, a multi-year AE, or even a VP. Not the best pay, and depending on the team/league you're working in, there's a lot of nights and weekends that require you to be working.

FinanceEngineer

Politicker

5

Sr Director, sales and partnerships

How does HR work when buying software? Are they as incompetent as with their normal role?

HappyGilmore

Politicker

2

Account Executive - SMB

It's interesting, I've had some folks from HR who have it together and have actually helped move things along quickly. Yet on the flip side, I have one HR contact specifically that is about as useful as a poopy flavored lollipop. Just absolutely terrified to help implement our software.

FinanceEngineer

Politicker

2

Sr Director, sales and partnerships

They either bulldoze the path or bulldoze you, sounds about right. Can you usually tell early on which bucket they will fall in?

HappyGilmore

Politicker

1

Account Executive - SMB

Yeah I'd say I can tell early on which bucket they fall in.
The more excitement they have in my experience the more likely they are to advocate for us, push internally. If there's hesitation they may try to block internally.

jefe

Arsonist

5

🍁

Awww man, I missed it!! Thanks for stepping up and sharing @HappyGilmore

HappyGilmore

Politicker

4

Account Executive - SMB

Great GIF choice! Happy to share as well. If you've got a question @jefe I'm happy to answer as well 🤠

jefe

Arsonist

4

🍁

I think everybody covered it, but I appreciate you!

I was most interested in the cross country move aspect, but @Sunbunny31 and @oldcloser beat me to the punch.

CuriousFox

WR Officer

3

🦊

I always think of Shooter 🤣

QWhiz

Tycoon

2

Founding AE / ex-SDR

I joined war room 6 months back. how was it 2.5 years ago? how has it changed over the past two years?

HappyGilmore

Politicker

4

Account Executive - SMB

2.5 years ago not too many changes I would say. A couple of big ones that I have noticed is there's less of a push to refer members into the WR, and I'd say a little less engagement from those who helped create the War Room.
Some of the original users of the WR are no longer using it as well (just based on who would post a lot previously)

unclespacejam

Politicker

2

ur dad’s brother

Where you at @LordOfWar ?

QWhiz

Tycoon

2

Founding AE / ex-SDR

who do you sell to in the hr/comms space? LnD? Or HR? A friend once said
HR never gets budget for tech (though they do get it for friday fun
activities)and always has to beg - and even then doesn't get it. How
true is that?

HappyGilmore

Politicker

2

Account Executive - SMB

More HR than LnD but on the bigger deals LnD comes in.
If it's purely HR asking for budget that's an issues, yet more often than not, IT is also tied to their software evaluations and they can help secure budget more quickly than HR can.

FranchiseSalesQB

Politicker

1

Franchise Sales QB

Moving cross-country and new everything is scary and ballsy but I guess thats what makes it exciting. I'm all about being open-mined, willing and honest with those you're well on your way.

AnchorPoint

Politicker

0

Business Coach

Sales is definitely a learned skill.

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