Who would you rather sell for? Market Leader or the Underdog? And, why?

I'd prefer the underdog because the sale just feels more rewarding. Always love a good hustle.

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49
CuriousFox
WR Officer
11
🦊
I'm going for the best product.

I've been on both sides. Sometimes the grass is greener, sometimes it's not. Go for the product. 
34fifty
Valued Contributor
0
Team Lead
That's a good way to look at this

CoorsKing
WR Officer
3
Retired King of the Coors Knights
Depends on what stage of the lifecycle the market leader is. If they are still early on (recent IPO, etc) and in the hyper-growth mode, market leader for sure. Name gets you in the door, lots of greenfields to sell. 
34fifty
Valued Contributor
0
Team Lead
Interesting. Considering that there are so many recent unicorns in the market. 
CoorsKing
WR Officer
0
Retired King of the Coors Knights
I work for a former unicorn so I am a little biased lol
34fifty
Valued Contributor
0
Team Lead
Oh yeah? Where did you learn the most from? The unicorn or your current stint?
CoorsKing
WR Officer
0
Retired King of the Coors Knights
Well I say "former" because we are some years post IPO now. I have actually been here my whole career, started as an SDR right out of college. I think I learned the most right around the IPO, the leadership at the time was phenomenal and great mentors. 
34fifty
Valued Contributor
0
Team Lead
Interesting. Have you guys managed to retain the same culture while scaling up? That must have been a challenge.
Tres
Politicker
2
Account Executive
Who has better resources? Does the underdog have what it takes to keep up? There's many factors at play, but seems like market leader would have the advantage for resources supporting the sales cycle. 
34fifty
Valued Contributor
0
Team Lead
Absolutely. But I've known a few SMB clients who preferred smaller business because they felt they got more attention.
MrMotivation
Politicker
1
Sales
Whoever has the better product, or game changing feature necessary for their industry. 
Blackwargreymon
Politicker
1
MDR
Depends on what stage of the lifecycle the market leader is. If they are still early on (recent IPO, etc) and in the hyper-growth mode, market leader for sure. Name gets you in the door, lots of greenfields to sell. 
Clashingsoulsspell
Politicker
1
ISR
Depends on what stage of the lifecycle the market leader is. If they are still early on (recent IPO, etc) and in the hyper-growth mode, market leader for sure. Name gets you in the door, lots of greenfields to sell.
Ace
Arsonist
0
CEO
Underdog because 1 reason that you mentioned and the other that there will be a lot to learn. Growing an underdog will also put me on the spotlight. I just hope I don't become one of those LI thought leaders after that 😂 jk
34fifty
Valued Contributor
1
Team Lead
Hahahaha. That's the epitome. LI thought leader :D
Salespreuner
Big Shot
0
Regional Sales Director
Underdog and make it a big deal by marketing and advertising about it via testimonials and stuffs

34fifty
Valued Contributor
0
Team Lead
Amen! 
paddy
WR Officer
0
Director of Business Development
It's more invigorating to sell for the underdog. Nothing like ripping and replacing a market leader. Looks great on your resume too
34fifty
Valued Contributor
0
Team Lead
Absolutely. The win just feels so much more fulfilling
braintank
Politicker
0
Enterprise Account Executive
The market leader is usually the market leader b/c they have a better product. I'd always prefer to sell the best tech. 
34fifty
Valued Contributor
0
Team Lead
What if the underdog has a product that's strong enough to compete, but don't have the marketing/sales resources to match the competitor?
braintank
Politicker
0
Enterprise Account Executive
I'd always default to whoever has the better product. There's usually a reason they don't have the marketing/sales resources to compete. 
LordOfWar
Tycoon
0
Blow it up
Underdog all day. Growth opp, less comp (internal and external), plenty of potential customer conversions from the competitors on review sites. Also, the bigger companies get the less they tend to comp sales savages like us.
34fifty
Valued Contributor
0
Team Lead
Interesting point about the review sites. 
Kiona
Opinionated
0
Head of Business Development
I would prefer to sell for the company that I believe is the best fit for the market. Sometimes that is the leader, sometimes it is the underdog. But you have to buy in to what you are selling or it will be a slog. 
34fifty
Valued Contributor
0
Team Lead
True. If you believe that your product adds value, the conviction shows in your sales pitch
Chep
WR Officer
0
Bitcoin Adoption Specialist
I'd sell for the company that was a better culture fit for myself 
BossBitch
Politicker
0
Account Executive
Currently I work for an underdog. We offer better support, a product that is growing and changing to meet the demands of the market, my exec team supports me on calls and shows up (unlike the market leader), and we win against them and get referrals. Market leaders get cocky sometimes and don't provide the service and flexibility that the underdog does, so i prefer the underdog. Plus it's really rewarding to win against them 🤩
makeithappencaptain
Catalyst
0
Sales Enablement
I've done both and like both. My preference is Market Leader (even better if it's pre-IPO because there's still growth!). Market Leader Pros: thought leadership, credible proof points, proof of RoI. But an Underdog that actually works is a fun ride. Underdog Pros: Being part of building something, nimble, could be an interesting buyer that legacy companies don't target, if the "underdog" is going places there's usually good career path for those who get in early
CCP
Opinionated
0
VP, Business Development
I think more important than the org is the boss and team. Especially where large orgs can have micro company cultures i.e. this branch is awesome and crushes versus that branch who looks for jobs all day and cry themselves to sleep every night. 80% of people leave bosses, not companies. 
Dorsiareservation
Good Citizen
0
Sdr, Outbound
Underdog (pre ipo) for the long term career progression and the feeling of landing the sale against the market leader
SDMHGWarrior
Tycoon
0
CEO
Underdog all the time.
DC540
Opinionated
0
Sales Development Manager
Underdog.  People doubting me is a great motivator.  I'd be happy to punch up if the product works, the leadership team is solid, and the GTM strategy is something I believe in.  
Cabbie
Good Citizen
0
AE (Account Executive)
Depends on the product, but also leadership tbh.

Worked for a market leader & currently with an underdog.

Market leader had a bang-up product, but was a bit rigid when it came to sales approach; and underdog has super agile, exciting leadership, and a product with a lot of potential, but still finding its feet on process & support.

Prefer the underdog though: agree with the others saying taking down Goliath is a total rush 💪 
34fifty
Valued Contributor
0
Team Lead
There has to be a balance between agility and stable processes. But finding that balance is a challenge that is fun
sugardaddy
Politicker
0
🍬
I have done both. Frist the Market Leader and later on The Underdog. 

I prefer to work for the underdog, because you can help shape the organization, the sales department and generally be more hands-on. Just my opinion
34fifty
Valued Contributor
1
Team Lead
True. Its better to be a large part of something small than a small part of something large.
JJASBE
Catalyst
0
Director, Solutions Sales
Whoever has the most well-resourced customer service team, and the most closely-aligned sales and marketing org....
breezyboiii
Politicker
0
Sales Boiii
depends on a few factors. But ultimately, whatever has the most opportunity for growth and success.
Sales4what
Opinionated
0
Co-Founder & VP Sales @ PLURiTy
Underdog if there product has competitive advantages, often the underdog will offer better perks 
34fifty
Valued Contributor
0
Team Lead
True!
SoftwareSlanginSavage
Good Citizen
0
Senior Account Manager
Depends on what point in my sales career im at.
Rigeyyy
Opinionated
0
Account Executive
Market leader. It’s fun to sell the best product and see how it can really help your clients 
ellewoods
0
Account Director
Underdog with a solid product I believe in and resources to keep innovating.
JuicyKlay
Celebrated Contributor
0
AM
I don't think it matters as long as your happy and believe in the product, your leadership, and the company.
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