What was Software Sales like when you started?

Let's dive right into the meat and beans here, SOME of you senior sales types are old as Abraham Lincolns pet Monkey Gabriel!


All jokes aside, my boss (who knew Gabriel) told me he used to drive to a hotel because they had a pay phone and dial straight from the pay phone with a bag full of quarters and a phone book!


First thought is why are people still asking how I got their number 40+ years later... neither here nor there...


But I am very interested to see what it was like for you all and other cool stories.


Because no way were you doing 120+ dials (rotary), 50 type writer letters daily!

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9
poweredbycaffeine
WR Lieutenant
4
☕️
My first professional job ever was actually in FinServ as an SDR. I was required to make 130 dials a day and sell 20 memberships to our lending programs each month. Could not leave the office with less than 130 dials, but they were all fed to us via a lead system and we did 3 major call blitz per day as a sales floor. I also had to analyze the deals once they bought the membership ($99), and then if they were qualified I sent them to my AE (picked up the packet and walked them across the floor). I had no financial background and I can't believe I was responsible for half the shit I did.

First SaaS job was as a BDR. 100 dials, 50 emails, 20 ops a month. Some months I hit 60 ops, some months I hit 10. Cold calling was brutal into F500 CTOs, but I learned how to be a friends with gatekeepers and how not to throw up when an actual CTO picked up. Social selling still wasn't a thing, but you could get into some good convos via Twitter (and book meetings via DM). Emails were all one-off, no sequences or cadences existed just yet. We did use Yesware to track opens, but it was so new that it was scaring even us as reps.
InQ5WeTrust
Arsonist
4
No marketing, mayo isn't an MQL
Ahh 2018, what a fine year. 

I remember it like it was almost yesterday. 
alecabral
Arsonist
3
Director - Digital Sales Transformation
When I started technology looked a lot different though thankfully, "the Internet" was already making some stuff possible, like web conferences (audio, no cam). My dial pad was physical, my CRM was a Lotus Notes spreadsheet and we used Eudora as an email client (before Outlook became the norm), way before gmail as well. No cell phones for anyone but the top reps, laptops were not possible and you were forced to work at the office. Every sales rep got a car expense fund but only directors got cars. 

Dashboards were crueler than today. No sentiment at all, just hard cold numbers. "Buyer personas" was not a thing. I had to talk to hardcore DB admins and IT managers, they kicked my ass around for like a year before I managed to get a hang of it. Those guys knew stuff they knew we didn't know and goaded about that. I had a sharp suit, because even if we were just SDRs you were supposed to go into the office wearing a jacket. I never wore ties, but my boss (an engineer, like his boss and our sales director as well) frowned upon me because of that. He had an IP phone (probably the first kind) and we of course just had those analog dial pads and an awful headset that put some unnecessary pressure on your temples. 
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
I hadn't thought of Lotus Notes or Eudora in years!
alecabral
Arsonist
1
Director - Digital Sales Transformation
ha there ya go, looks like we're part of the same generation!
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
It's been so long, I've forgotten so much.

Remember ICQ?
MCP
Valued Contributor
1
Sales Director
Slack forerunner.
alecabral
Arsonist
1
Director - Digital Sales Transformation
LOVED ICQ!
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Oh gosh, I do feel like an utter dinosaur.   My laptop weighed a thousand pounds, dotcom was just becoming a thing, and we didn't really even outbound - we were really busy with inbounds.   I fell into the industry because I was just looking for a job, and ended up with a receptionist ("Assistant Office Manager") position with an ASP, became the Office Manager within months,  transitioned into Sales Coordinator because my CEO liked my phone voice, transitioned into sales because our AE didn't want to handle the little things and I started closing business he didn't want.  Became a field rep in just over a year after starting, and actually started getting some training when our company merged with another before the end of the century, was wildly successful for a couple of years, and then the bust happened.     

Does anybody remember the phone company Iridium?  My boss was considering one of those rather than the flip cells to replace his Blackberry.

I also remember the first iteration of Salesforce.
alecabral
Arsonist
1
Director - Digital Sales Transformation
I wish you had a capture of that first experience with Salesforce! I only became an user in 2011, which was freaking 10 years ago!
Sunbunny31
Politicker
0
Sr Sales Executive 🐰
I had no idea it would matter so much!   I was able to walk into my next job in the very early 2000s once the tech companies were hiring again, take a look at a rudimentary Salesforce CRM, and recognize it.   
sdrgod
Opinionated
2
Global Leader, SDR and ISR
Only 5 1/2 years ago Id have prospects FREAK OUT at an opex concept. They steadfastly refused to accept it.
MCP
Valued Contributor
1
Sales Director
Shrink wrap agreements. Had to include a line item for a media kit. Lotus Notes, certainly no LinkedIn. Siebel with 1000 fields per page for CRM. Printed out call sheets.
Diablo
Politicker
0
Sr. AE
I joined SaaS when the industry got matured but it's so fun to read all your experiences.
cw95
Politicker
0
Sales Development Lead
People really had no idea what my industry sell and really didn't like the thought of it...3 years on and the competition is as high as ever. 
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