The War Room

SaaS Sellers - Is Enterprise where its at or Scaling Start-up?

Having worked in a different size SaaS Business from Large Enterprise to Bootstrap Start-up, I see the benefits of all. Whats your opinion on the best space for sellers to cream that πŸ’΅ and why?

Big ticket, long sales cycle Enterprise solutions?

Steady but competitive Mid Market solutions?

Small agile, niche solutions that can fly through procurement?

πŸ‘‘ Sales Strategy
πŸ“ˆ Closing
πŸ’° Compensation
Sales Director
I've definitely had better experience working mid market rather than enterprise. This is because a tonne of Saas companies hire enterprise AEs and believe that their product is enterprise ready when it's definitely not.
SDR Manager
Echoing this!
CEO - Overheard_Sales
I like mid market. Big Ticket can leave you with a $1M year or a base salary year haha
Strategic Account Executive
gotta have enough accounts to work to keep enough balls in the air. working in enterprise sales with pre-defined books can be a real nightmare.
WR Lieutenant
Account Executive
I prefer scaling a small startup because the comp plan is not figured out so you can smashhhhh the quota and claim the best accounts
Notable Contributor
Regional VP
Enterprise is a grind with those long sales cycles, but man it's such a high when you close a big one you've been working on for 9+ months...
Commercial Director
Ye i think that was a thing for me Enterprise is like living with manic depression for 9 months then its like you've dropped ecstasy when the contracts signed! Its not the healthiest lifestyle but an unbeatable high!
WR Officer
Business Development Team Lead
As someone who has been in sales for 1 month less than that I'm sure it's a rush
Director of Sales
I think Mid-market is the sweet spot, personally.Β 

Normally a good basic and the chance to do a few deals a year and make good commission.
Account Executive
I think you answered your own question.

”I see the benefits of all.”

Pros and cons with all avenues. Depends mainly on what you’re looking for in your career.
Call me what you want, just sign the damn contract
There are solutions that fly through procurement? Tell me about this wizardry. But yeah, I like mid-market plays myself having done all 3.
Notorious Answer
Account Executive
Equity... Unless youre willing to put in 20 years at a massive tech company, which you'll have to do to make any kind of serious (serious) cash. Equity is where its at. I once worked with a VP of product marketing who never stayed more than 2 years at a company as that is when the bulk of your equity will vest. He is absurdly well off with homes in NYC and the French riviera. The sales will net you tons of money if you get in to the right territory at the right time, which is pretty true across all of the size options. But the equity make a huge difference. It can be risky, but joining ~150 person start ups with really good investors (sequoia, svh, etc..) can net you massive lump sums within 5 years.

Good Citizen
Enteprise Account Executive
I would say ENT is where you make the most... Have the most fun in SMB/MM... Done both SMB is like constant small highs... ENT is like starving for a year followed by the feast of a lifetime... over all you'll make more money in ENT. But it also sucks the most... think 300+ calls/demos/pocs/negotiations/msa/DPA/Legal call to get one deal done...

I think it is more personality based. One of the absolute best reps I ever knew preferred to work SMB. He worked enterprise for all the big names; oracle, SAP, Workday in its early stage. Came to work at the company I was at 4 years ago strictly to work SMB-MidMarket because it was better for his emotional health. The quick wins made him feel better than the long drawn out enterprise process. He sold more in ARR than three of our enterprise reps in the time I was at the company. They paid him accordingly.Β 
WR Officer
Senior Account Executive
I personally like the challenge of Enterprise, but you may like mid-market.
Fire Starter
it's all about that product-lead, self-serve model!
Big Shot
Account Executive
I’ve loved the energy of closing smaller deals and consistently. Instant gratification, there.Β 

Going to be handling enterprise now. Wanna test out those waters and see how I feel.Β 
Client Director
I faced this question after spending the last 3 years in enterprise sales.Β  I had an offer from Hubspot where their sweet spot truly is the mid-market.Β  Low base but sky high OTEs with reps well above 100% regularly.Β  I ended up taking another offer to stay in ent sales and the long sales cycles always makes me think about what would have been at Hubspot with the fast and furious pace.Β  At the end of the day I had to stick with the higher base as a new dad less wanting to take risks.Β 
Good Citizen
Key Accounts
Enterprise/Strategic in legacy firms or selling whatever in an hot/buzzy start-up in a high-growth market. The in-between Mid-market segment is mediocreville to my line of thinking, and I'll tell you why:

The only way I've seen IC's be 7 figure earners is to sell big tickets and smash quota with an enterprise deal or sell the new shiny toy while vesting RSU's monthly...and IC's only get RSU's in start-ups generally.Β 

Slinging mid-size deals in a volume play to get to accelerators on a mid-market comp plan is thinking too small, for my tastes.
Account Executive
This thread is interesting. As a mid market rep, I’ve thought my next goal would be ENT but maybe the grass isn’t greener
SaaS Seller OTEs
SaaS Sellers- Move on or be patient?
Move on/ Be patient
verbalzzzzzz , Β  BCD , Β  sam Β  and 23 people voted
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Enterprise AE Comp - SaaS Sales