Whale Hunter Advice

Hey Sales Savages, got a question for you. Maybe I am misguided, I'm not sure, but my gut tells me I need to change up my sales strategy. I'm entering my third fiscal year at a SaaS startup. This last year, I made club and hit 140% of my number by closing 19 deals and 8 new logos. That said, my average deal size was around $100k per deal which is lower than the company average. The largest deal I closed was $650kACV/ 1 year. As I look around at the company, despite this solid year, I see reps closing 2 or 3 massive deals a year - several 7 figure deals closed at the end of the year from reps who arrived later than I did. It's easy to compare myself to their larger deal sizes, and I'm wondering if I should cut the transactional mindset and move into a far more strategic/enterprise format. Longer sales cycles, but larger deals and less land and expand.


Is this a good idea and if so what are the things you've done to shift your mindset to a whale hunting mentality? How do you get by during the months where nothing closes? Is this just my ego talking, or do I need to shift things?


Thanks for any advice

👑 Sales Strategy
9
braintank
Politicker
7
Enterprise Account Executive
More at bats is always better.
CuriousFox
WR Officer
3
🦊
🦇
antiASKHOLE
Tycoon
5
Bravado's Resident Asshole
More meetings = more opportunity is going to be the general consensus.
I would suggest maybe reaching out to those reps and see what it was they were doing to land deals that size. Take what they say and use a “shopping cart” method of what could work for you right now.
TennisandSales
Politicker
3
Head Of Sales
so do you NEED to go after bigger deals? o mean you crushed your number!

Also your would need a big mind set shift. because you could go a number of months without closing anything when going after big ass deals.
I would talk to those reps that closed the bigs ones. go see what they did to find them and close them. Are they also closing smaller deals? are they exceeding quota more than you?

bigger is not always better. especially when you doing well.
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Pros and cons to fewer big deals vs volume. Of course, the biggest one is if your quota is tied to 2-3 deals, and one slips, there goes your year.
However, the big question is, do you feel like you're leaving money on the table by being more transactional? Do you think you can continue to bring in 15-20 deals/year but increase the deal size a bit?
Finally, have you talked to your peers about what they're doing? Or your manager to see if there are any concerns and/or recommendations?
Congratulations on the excellent year!
HVACexpert
Politicker
3
sales engineer
It’s your territory. Don’t get caught up in “seeing how green the other AEs grass is”. If seeking more smaller jobs is what gets you to your quota then do that! Unless you have some company push or KPI for larger $ per sales then don’t worry. You’re killing it King, keep doing you.
Pachacuti
Politicker
3
They call me Daddy, Sales Daddy
Whale hunting strategy - always have 2-3 whales you are hunting which will buy you the boat &/or vacation. But remember that you'll pay the bills with the tunas.
saasesforthemaases
Tycoon
1
Account Manager, West
great advice, thank you.
yosoybill
1
Account Manager
If you make the shift, you’d likely want to get a great idea of the average sales cycle for those deals. You’d also want to look at your own territory and see if you have the potential buyers for large deals. If yes to that and have a good idea of the cycle, just ensure you have runway to get to closing business before people start asking questions about why you’re off your quota.
saasesforthemaases
Tycoon
0
Account Manager, West
Just wanted to say thanks to everyone for all this exceptional advice. I've actioned on almost every single comment this week, including a strategy discussion with my boss today around how he'd like to see me proceed and what leeway I'd have if I solely moved to giant logo acquisition. Really appreciate everything here. Thank you.
ChumpChange
Politicker
0
Channel Manager
I've always had greater success with quick wins. Boosts your confidence, puts your name on the board, more convos, more use-cases, more pain points, and more exposure to the customer pulse. Those benefits end up transferring seamlessly when you hit the big leagues. No shame in your game. Keep hustling.
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