AMA: Hopping with Sunbunny


TLDR: I’ve been around a while.


Honestly, I’m honored to be asked to contribute an AMA; thank you @Gasty . I’ll try to keep this brief (haha) and not answer your questions in advance. Also, writing this out is making me feel really, really old – and I’ll be the first to assure you all, I do not feel as old as I may seem.


My sales career started before the end of last century (see, old), when I was moved into a “Sales Coordinator” role at a tech start up I’d joined as an admin assistant, because my CEO thought I had a good phone voice. I didn’t want to move into sales; it wasn’t honestly something I’d ever considered as a role or as a career, so it was a big decision. It beat being office manager, though, so I took the chance. And this would actually prove pivotal: we sold software as a service. At the time, we were categorized as an ASP, or Application Service Provider; basically SaaS before some bright person coined that term. From there, I started closing business and moved up into an AE role; as a company, we merged with our biggest competitor, expanded our reach, changed our name, and things looked golden! I have to say that had bandwidth been what it was to become just a few years later, I could be sitting on FB founder money, but alas, that was not to be; we were far too early out of the gate. Foundational technology wasn’t up to what social media would become. Instead, the dotcom crash followed by 9-11 led to layoffs; I’d been the last one standing on the West Coast in a spooky, mostly empty, office we’d been subletting to other companies.


Job hunting took a long and frustrating year, but I finally landed an awful role at a terribly-run Ed Tech company. Sometimes beggars cannot be choosers, and it got me back into tech sales. On the positive side, this purgatory led to a networked opportunity for a significantly better role with another startup – and they liked the fact I already had ASP experience. Honestly, this turned out to be some of the best times in my career with awesome colleagues and great, smart management. We were acquired a few years later by a major tech company, and that was the only time I’ve successfully gotten an equity payout (hello new car). I stayed for an additional 10+ years. Over that time, I was in a number of different roles and teams; sold quite a bit of martech software both in and out of my comfort zone. Went through the 2008 recession with some belt tightening and again through 2020. Had mostly good managers, one notably bad one, one great one, but several bad sales plans later, I jumped to where I am today, a smaller, privately held company where I am among a handful of reps and am working strategic accounts.


I’ve never been in sales management; I’ve never been a BDR (that role also did not exist when I started out). I’ve never sold anything but tech, unless you count Girl Scout Cookies and World’s Finest Chocolate. My industry literally did not exist when I was in college – and I would have thought you were nuts if you would have told me what I’d be doing less than 10 years out of college.


So go ahead, AMA. Results not guaranteed. Will depend on my mood.


🏰 War Stories
☁️ Software Tech
🤴 AMA
29
CuriousFox
WR Officer
20
🦊
YAAASSS QUEEN GET IT WITH YOUR AMA!!!

Thank you for sharing your story. I'm damn near convinced we are related. Our stories align so damn close bb that it's blowing my damn mind.

Also you are not old. You have fought life, and you have triumphed. I'm proud of you my friend. 🦊❤🐇
Sunbunny31
Politicker
13
Sr Sales Executive 🐰
Absolutely love this gif - definitely how we do it!
jefe
Arsonist
4
🍁
Every time I think Foxy can't post a better gif, I see something like this
CuriousFox
WR Officer
4
🦊
I'm gifted what can I say 🤩
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
GIFted! I see what you did there.
antiASKHOLE
Tycoon
12
Bravado's Resident Asshole
First Question. Who is your favorite snarky mfer in the WR?
Sunbunny31
Politicker
8
Sr Sales Executive 🐰
How much money you got?
antiASKHOLE
Tycoon
7
Bravado's Resident Asshole
About tree fiddy
Sunbunny31
Politicker
6
Sr Sales Executive 🐰
So far you’re winning.
medhardwaredr
Opinionated
5
Director of Sales NA
Ha! Luv it
unclespacejam
Politicker
3
ur dad’s brother
Okay I got 351. How bout now?
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
I've got time to hold out for more, but your bid has been registered.
unclespacejam
Politicker
3
ur dad’s brother
352 final offer
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Have received a sealed bid...sorry, bud. Not even close.
antiASKHOLE
Tycoon
3
Bravado's Resident Asshole
How about 69420?
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
How about it?
Filth
Politicker
4
Live Filthy or Die Clean
@Sunbunny31 do I mean nothing to you?
antiASKHOLE
Tycoon
3
Bravado's Resident Asshole
You are just filthy though. I think that says enough.
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
The very world. I’m hurt you even felt you needed to ask.
wolfofmiami
Opinionated
4
🐺
Definitely up there
TheQueenofDiamonds
Politicker
10
Account Executive
You are legit one of my 2 favorite ppl here Love your story and hope you keep rocking and sharing your experiences Sending good vibes
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Oh, my heart. ❤️. Thank you.
oldcloser
Arsonist
8
💀
I freaking love your story. ASPs!!! As perhaps (or no doubt) the elder in this crowd, here’s my takeaway. Stability. Very few career moves in a world where new folk almost have to make them for one reason or another. That you still own the first new car you ever bought. That your daughter drives it now. That you still live and work in the same community you started in. All of this

Stability personified, with success all over it. I’m so freaking impressed. It’s totally consistent with who and what you are in here, reliably accurate and always thoughtful. This story and the person attached to it are exemplary, not just for new sellers, but for all of us. So glad you shared it.

Question time: What would it take for you to consider a career change right now, this moment. You get the rest of the week off, and start the new one Monday morning.
Sunbunny31
Politicker
7
Sr Sales Executive 🐰
Interesting observation about stability. As an AF Brat, I spent most of my childhood moving from place to place. I probably had a “been there, done that” look by the time I was 11.

Pragmatically, the one thing required for a career change would be sufficient money. Like a lot. Like winning the lottery amount. Because there isn’t anything that pays as well as sales that would enable me to leave it all behind and start something new. If money was not a factor, would I change careers? Maybe. But not sure what else I’d do that enables me to travel, meet people, solve problems. I’ll have to think on it.
snacks
Opinionated
7
AE
No questions, just here to stan. 😍
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
It’s an AMA….doesn’t have to be about sales. :)
NoToBANT
Catalyst
6
Senior Account Executive
No question but just wanted to say I thoroughly enjoy your content
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Wow, thank you. That means a lot.
bonez
Politicker
5
Account Executive
What do you think has changed culturally about tech sales since you've started? You've seen most of the big pivotal moments so I'm curious what has remained the same and what has changed?

Follow up to the question you just read - what would you like to see changed or come back?
Sunbunny31
Politicker
7
Sr Sales Executive 🐰
This is going to come from a highly individual place of observation, but I think what used to happen in tech was a sense of collaboration and community. No need to build a “family” - you just tried to find ways to work together. Many hats worn in early days; sales partners working together rather than a lot of rules. It was uncharted territory, and in some ways, it felt like we were making it up as we went. In what other world would you take a brand new sales rep, with no sales training, to Chevron, to pitch? Or get to hop on a plane with the company’s investor to head up to Amazon for a chat with Jeff Bezos? Tech was new, it was fun, and there was enthusiasm.

Today - sales processes, sales tools coming out one’s ears, sales trainings, over saturated sales teams, multi-level sales management - all common. Now, if I could take what I know now, go back in time to that first company, I would absolutely crush. I did finally get some formalized sales training; it reinforced some of what I’d picked up from my first sales manager (who became a friend); I’ve since had more. And had to leave a Keenan training when I realized how much of an outlier I was to all the fresh young reps at the company, and that I would suck the life out of their learning. But I digress.

What would I bring back? The optimism. We were breaking new ground, and it was exhilarating. There really was a “can do” attitude in the start up culture that I think has been erased by cynicism.
unclespacejam
Politicker
3
ur dad’s brother
Damn I really wish I could have been working at this time. Shit sounds like a ton of fun
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
It was - but there were also a LOT of companies that focused on "eyeballs" rather than "revenue". That was bound to come crashing down, and did. It wasn't supportable long term.
bonez
Politicker
3
Account Executive
This was a great read. Totally feel you on cynicism in the tech space now. I feel that when something becomes commonplace it develops cynicism instead of wonder or excitement.

Let me ask you this, how did you weather all of the economic ups and downs? Did you become more strategic financially? Sell a kidney? What was/is your secret sauce?
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Don't spend money you don't have.
And in the first downturn (dotcom crash and 9-11), I couldn't land a tech sales job to save my life. I had just had a baby, we just bought a home, timing absolutely could not have been worse. But there was also a fair amount of suckitupbuttercup. I went back to waiting tables to augment my (laughable) unemployment and managed to scrape through that year. I got that woeful edtech job, continued to work nights and weekends at the restaurant, and busted my ass for another year until I finally got the great job that has led to so many good things. Not going to lie, those were two very tough years, but if you have the capacity and willingness to just buckle down, you can get through anything.
2008 - wasn't actually terrible in my sector. Not great, but wasn't awful.
2020 - was bad, and it followed a terrible year because of a bad go to market plan at my employer, where they whiffed completely. Savings depleted, and I'm still building back from that. College and grad school kids are no joke.
That said, sales is full of highs and lows. Treat yourself in the highs, but know the lows are coming, and don't overindulge. Save.
bonez
Politicker
3
Account Executive
Love everything about this. This is so important for anyone in sales to read. This is what the journey looks like and some years you're balling like crazy and others you're scraping by. Savings are key.

The tough years definitely sneak up on you and they always seem to happen when you have a kid and/or buy a home... That's been my story too at least. Thank you for this.

SO great reading your journey. Helps me feel validated in the rollercoaster that mine has been at times too. Really appreciate it again.
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Timing inevitably sucks! But yeah, prep for the lean times during the boom times - you just never, ever know.
Diablo
Politicker
5
Sr. AE
Wow, lovely story. How do you manage stress and balance your work & social life
Sunbunny31
Politicker
6
Sr Sales Executive 🐰
Thanks, Diablo. I'm fortunate enough to be a remote employee, which definitely helps with the work/life balance. It took a little adjusting at first, mostly for the family (husband) to understand that me being at home didn't mean I could, or would, take care of chores. Now, that doesn't mean that I don't pop down to the laundry room and start a load, because I do, but I hazard that at this point, I've gotten very efficient and don't waste time doing things that can wait. And everyone else is trained that if they leave something in the sink, it will most likely be there when they return.
When it comes to work/life balance, it's largely related to very efficient time management and the ability to sort out schedules. Again, having the ability to work remotely gave me a ton of flexibility with my children when they were younger and needed to get from point A (school) to point B (practice) where ever that was. Now the kids are both out of the house, and although I'm still working with a sports schedule for the college student, my house calendar is not nearly as jammed up as it used to be.
As for stress, I do my best to practice patience. I go out for long walks when I can; I live near a nature preserve and can walk to it and through the trails when the weather permits. I step away from the computer. I do not eat lunch in front of the computer - I take a real break/ And finally it's another reason I am glad I'm remote: If things come to a head and I need to vent, I can swear like a mf and nobody is here to hear me but the cats, and they do not care. Get it out of my system, move on.
Diablo
Politicker
3
Sr. AE
These are such good pointers, love it. Amen!
Filth
Politicker
1
Live Filthy or Die Clean
"... mostly for the family (husband) to understand that me being at home didn't mean I could, or would, take care of chores" is my current issue when I work remote. My wife has told me it's actually worse when I'm home v at the office and that bugs me so much b/c I'd love to not do the (short) drive and have an actual openable window.
Still trying to figure my way through this with her and remote...we do have the 9mo old and 3 school aged children so I may be at a loss and on this one.
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
That’s a tough one. Is she currently a SAHM? Or are the kiddos in child care?

Obviously mine are older and needing parents in different ways (mostly the wallet-ways), but my husband, bless him, works at a golf course, and with the weather being what it is, he is home All. The. Time. And he has a slight resentment of me working, though it only manifests through him playing his binge TV a smidge too loud in the adjoining room.

With the kids and SO, it is a matter of balancing what’s going to keep the peace vs what’s going to pay the bills. If you can peel off a few minutes here and there to give her a bit of a break or have lunch together, it will go a long way. I’ve gone out to lunch with my husband a few times, and it has been beneficial.

But a fuller opinion will come after I understand your current situation better. I will say there are no perfect solutions, but also this is not permanent. Those kids are going to age and things will naturally change.
pirate
Big Shot
5
🦜☠️ Account Executive
Ah AMA I have been looking forward to. You know you mentioned admin assistant and I just thought of Donna Paulsen in Suits. "I am Donna and I am awesome". Your story is pretty inspiring. Is there anything you do that helps you build a mindset and resilience and being so adaptive with all the changes (9/11, recession, different roles and different teams) ?
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Aww, (or arrrrhhhh?) thank you!
Honestly, I've always been a "things will always work out" kind of person. So I have that underlying optimism that I think you are born with and don't acquire, so the experience of others who are by nature more pessimistic or cynical may be very different.
And going way back, I'm the oldest of 5 kids. We certainly didn't have much, but it always seemed like it was just enough. But I did have to power through not having a new car ever, not living in the best neighborhood or biggest house - we just didn't have those things. I was told there was no money available, and I had to put myself through college; my parents thought it was important, but it was just out of the cards for them to provide the tuition. So I did what I could to get into school, and was fortunate enough to get a full ride based on academics. It was really my first introduction to goal setting: know what you want, and find ways to have the best chance at getting it.
And different roles/different teams: things didn't get terribly boring when you don't really know what the new FY will bring. There was always something to learn, and outside of that one manager, I worked mostly with truly outstanding people. There were a couple of years where I'd literally be underutilized (bad sales plan, confusing go to market strategy) and would help out other teams on the side with things I knew how to do quite well. That didn't really help my $$, but it did help with internal good will, so paid off in other ways downroad. I may have stayed there a few years too long, or maybe not. I ended up somewhere good without having an interim step of somewhere not so good, so I guess I cannot complain.

Finally, resilience is an interesting thing. I believe that some of us are simply more prone to having resilience; for others, it takes practice and focus to acquire the skill. There's a great book out there called "Grit: The Power of Passion and Perseverance" by Angela Duckworth; there's also a video, I believe a TED talk, by her. Strongly recommend, as it provides a good deal of insight.
Thanks for asking!
pirate
Big Shot
1
🦜☠️ Account Executive
Thanks for replying! And thanks for sharing how you think. I got the book and have watched the Ted Talk too
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Kindred spirits! I was fortunate enough to see her speak in person. She is very interesting!
wolfofmiami
Opinionated
4
🐺
What car did you get and what do you drive now. I’m getting Tesla model Y vibes
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Tesla was still a glimmer at the time, and I had very little equity. It was my first new car ever, though. I’d always bought used - though I still miss my 924. That said, it was a Honda CR-V. I still have it - over 200k miles on it! That car went just everywhere, and was perfect for my family. My daughter drives it now.
Sunbunny31
Politicker
5
Sr Sales Executive 🐰
Oh shoot - didn’t answer the second part of your question. Believe it or not, I got a second CR-V. It’s the top of the line one - leather, sun roof. They’re just great cars. We have a 370Z and BMW wagon to round things out.
wolfofmiami
Opinionated
1
🐺
My ex drove one of those, thanks for making me think of her. 🥲
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
Bwahahaha. Totally unplanned.
antiASKHOLE
Tycoon
4
Bravado's Resident Asshole
Have you ever found yourself just chasing the carrot during your career?
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
ALWAYS CHASING THE CARROT.
I mean, what else is there?
Maximas
Tycoon
3
Senior Sales Executive
A long nice story full of success and determination,just didn't realize that you are that experienced back to the 90s,Keep it up!
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Thank you.
HVACexpert
Politicker
3
sales engineer
One of the best ones in the WR, you provide a ton of value here and I for one am grateful for your presence. Love and respect to you.
To piggyback off of @Diablo a little, when your children were smaller how did you manager your work/life balance? Any tips on how to keep on task at home and work and make sure everything that needs attention gets it?
My wife and I both work with two small ones now, so it gets a little crazy and I always feel like I am running around like a chicken with my head cut off.
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
So when my little ones were very little, I went to an office, so they were at preschool or in home day care. Unless they were sick, I wasn't at home (office was in my town, which was awesome). When they got to be elementary-aged, they went to aftercare and I'd pick them up later in the day so I could have a workday without kids underfoot. Work was a bit of a reprieve in a way, but it was also great to come home to kids and their energy.
Once they got older, that's when it was a blessing to be able to work from home. Getting them to and from their activities was awesome; they both stayed busy with things like sports and band, so it was mostly managing a taxi schedule, but having the luxury to be available for 30 minutes around 3 pm, when that wouldn't have been possible if I was in the city and commuting. Friends of mine that did commute built out networks and shared taxi duty.
On task at home: some things you have to let go. Maybe you won't always have all the fingerprints off the windows. Maybe some toys don't get put all the way away every night. It was hard for me to not stress about cleaning up, but there are only so many hours in the day. The house wasn't a pig sty, but I was never going to be featured on House Beautiful; we just don't live that way. Do set aside time for yourself or your hobbies. My last home had a rose garden I built out and maintained. This meant a fair amount of pruning and tending. Once a week, I was in the garden. The kids were running around, but I was taking care of something I enjoyed. Fortunately, I enjoyed their activities for the most part, so my entertainment was Little League games and cheer competitions, and the local county fair horse show. We stayed busy, that's for sure. It's really fun to see what they gravitate to and what sticks.
You will feel a bit like a chicken with your head cut off. There's no way around that - but the other thing to remember is it goes by faster than you think it will. Embrace the chaos a bit. Be kind to yourself (and your partner) about missteps. Savor the moments; be in the moment. They are fleeting!
jefe
Arsonist
3
🍁
Thanks for always sharing great content, Bunny.

I remember you mentioning the other day some advantages and disadvantages to being a woman in sales, especially now that you're middle aged.

What has been your experience as you moved through a couple of decades of tech? Have you had issues with the boys club? Has changed at all over the years?
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
Interesting question. And a quick preface: the comment about being invisible is with regard to every day life. Middle aged women just…aren’t there. We’d make great spies because we aren’t really seen. That said, when I’m working and meeting in person or over Zoom, I am definitely part of the conversation and I see many others of a certain age also involved. So it s definitely something that happens when I’m out in the wild, so to speak.

But back to the beginning. 25 or so years ago, there simply weren’t that many women in sales. I was one of a very few. I did ok with the boys club for the most part. I like sports, I ignored goofy behavior, and could deal. We would joke about making sure we didn’t get our VP in trouble with HR, but a few bad jokes are not a big deal. And honestly, I’m pretty blunt and outspoken. I’ve scared my share of colleagues.

But.

There was one time with the first company, just after the merger, where the other woman was given a reissued laptop, that had originally belonged to HR. And it hadn’t been purged. And on that laptop was an .xls with salaries. And our two male counterparts were being paid $20K more/year than us. Yes, something was done. It was corrected. Apologies were given (they’d classified us as inside and the guys as field: claimed it was a mistake). But boy, was that eye-opening.

Another moment was with the large tech company before the 2008 bust. Combination Sales/Marketing conference. And after the first general session, everyone stood up to head to sales or marketing breakouts. And with a handful of exceptions, the women headed for marketing, the men headed for sales. That has definitely changed over the years. There are more women managing, being sales/solution engineers, strategic sales. It’s been a good shift. I’m sure there’s still a boys club - we’ve all read the news and seen the stories - but many companies aren’t fostering them as much. It’s the end result that is important.

Overall, I believe things are becoming more equitable in tech sales. Progress is happening.
jefe
Arsonist
2
🍁
Re: the preface - I figured that's what you mean. I'd imagine you're a force to be reckoned with in the workplace, and ignored at one's peril.

Thanks for sharing. It must be quite something to have witness such a stark change. Glad things are becoming better
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Of course it's all personal and anecdotal, so YMMV.
And yeah, I try a softer approach, but I've learned to hold others accountable for delivering what I need, and I'm insistent.
DionysusClytemNe
Valued Contributor
3
Account Executive
No questions from me other than please continue posting? Thank you, great content
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Appreciate that - and hope you’ll do the same.
HappyGilmore
Politicker
2
Account Executive
One of the best on here, thanks for doing this AMA and sharing your story.
As someone who was in MarTech as recently as 2 years ago, during your time being that vertical and selling that software, what did you like/dislike about that industry?
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
Well, I'm still in martech. The key to at least having a shot at job satisfaction is to have a foundational technology that is just about a requirement. Then everything else falls into place; you're going to be competing for sure, but you don't have to generally defend against nice-to-have vs need-to-have.
Dislike? Any time I'm dealing with a technology I can't answer the question: why you/why now? If I cannot get my head around the reasons someone would acquire the tech, I know it's going to be a huge challenge.
HappyGilmore
Politicker
2
Account Executive
Great point around the nice to have vs. need to have as I feel like most MarTech is a need to have.
One more question I had for you is in your experience, what items encompass a bad sales plan?
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
Limiting territories and what's in the sales bag; really reflected by the push oversaturation by sales teams. Misunderstanding the sales cycle and projecting based on faulty data. Misunderstanding the ICP and basing territories on that. Basing territories and plan on non-existing companies in the CRM. Basically, handcuffing reps into limiting roles where they have no way to make their number because what they're selling into isn't real.
JWA
Personal Narrative
2
Business Development Manager
Cool to read about your story. Thanks for always contributing your thoughts to my posts. I appreciate the perspective.

If you could learn any language instantly, what would you pick?
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Polish.
peachykeen
Politicker
2
sae e-commerce
No questions, Queen 👑 Great story, thanks for all your wisdom here 🙏
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Thank you! I hope to continue seeing you around as well.
Gasty
Notable Contributor
2
War Room Community Manager
clearly the best in-house AMA we've done so far @Sunbunny31
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
Oh wow, high praise. Thank you!
RandyLahey
Politicker
1
Account Executive
What a treat this is. A true OG of this place.
Sunbunny31
Politicker
1
Sr Sales Executive 🐰
I missed being an actual OG by about 6 mos. 🤷‍♀️
13

Job Hopping

Question
21
22
Members only

Job hopping?

Question
45
10

AMA with @FinanceEngineer

Official
10