The Latest from SaaStr: How To Succeed at Enterprise Sales

We’ve talked a lot on SaaStr about the damage a bad VP of Sales can do.  They often make things much worse than things were before — and burn a year and half of your capital doing it. 

It’s always better to have no VP of Sales than a bad VP of Sales.

But what if you are struggling to just find a Good/Great VP of Sales … should you hire an Interim one? 

These days, with more and more SaaS veterans out there, many aren’t quite ready to go truly full-time again, not just yet at least. 

But they are OK doing an interim role for 3-6-9 months.

But should you hire an interim VP of Sales? 

Or just put all your energy into finding a long-term hire? 

Interim, of course, is never really as good as 100% full-time, 100% dedicated, 100% all-in.  And we often defocus a bit from a full-time hire when we have an interim hire in place.

I think the answer is yes, sometimes.

So you’ve nailed your pitch for startups and are looking to hook your first mid-market customer. But suddenly, the buyer is a bunch of different people, and they want a bunch of new features. What do you do? 

Vanta’s Chief Revenue Officer, Stevie Case, shares lessons learned from leading Twilio’s mid-market team and shepherding Vanta into a mid-market leader as the company’s first CRO. 

Case shares the playbook for the “messy middle” to prevent the very predictable problems you run into in the middle ground of the mid-market, that space between SMB and enterprise. 

This edition of the SaaStr Daily is sponsored in part by SAP

The key to success in any business is growth. Growing your bottom line. Growing your operations. Growing your culture.

But sustained growth requires the right blend of forward-thinking management, intelligent cloud-based technology investments, and strategic financial planning.

Attend the Growth Summit hosted by Fast Company, Inc. and SAP on March 21

If you haven’t done enterprise sales before, the biggest thing to understand: you can do it.

But, you’re going to have to hustle.

Really, really hustle.

Many founders want the customers and leads and users to come to them.

They want to focus on the product, then on the funnel, A/B testing, optimization, SEO, SEM, etc. etc.

That’s all great, and for self-service business, that’s most of it.

But for enterprise sales, you’re going to have to get your arse out of your home office and go close some real live human beings.

• Listen — often in person. That often includes flying somewhere. It may include flying a lot of places, in fact, that you don’t really want to go.
• Learn your prospects’ business processes in detail, and how your product enhances them. If this is boring to you, you will fail.
• Learn how your potential customers will excel in their companies through your product.How can you help the career of the person buying your product? It’s not just about your fabulous UI/UX.

It’s a bit odd, because you want the CEO’s incentives to be aligned with the whole company’s, not just her or his individual efforts.

An annualized bonus for meeting the stretch plan is a great idea for a CEO.

But not a deal-by-deal commission like a sales rep.

It’s a bit of a flag of someone not going big, of not seeing the real win in their equity, not just in a short term contract or two. A CEO who optimizes on short-term comp never really goes the distance.

But still — I did it once.

Once, when the economy was in the dire straits it was in during ‘08-’09, and it looked like the world was over.

I went to several of our big customers, and asked them to pay more then, and to pre-pay up front. Even though their contracts weren’t up.

And they did it. All 3 of them. It basically brought in enough cash to fund us for the better part of a year, given our low burn rate.  Another almost $400,000 in cash.  That wasn’t for the most part due for almost a year.

Ok, get EXCITED for SaaStr Europa 2023, this time in London!  We’re looking forward to hosting 4,000 SaaS founders, execs, and VCs in hip East London at Tobacco Docks across 2 packed days, 6-7 June.

About 70% of our sponsorships are sold out, but we’ve got some good stuff left!

• 1 Super Gold
• 3 Gold
• 1 Platinum

And some really, really good ancillary and related sponsorships are left:

• Registration (this is a good one — do this)
• Braindates and Mentorship (this is a good one)
• Coffee
• Cantina
• Swag Store
• Founders’ Dinner

Up Next: Wednesday, March 22nd @ 10AM

Topic: Scaling The Top SMB SaaS Companies: What It Takes with GGV Capital 

Speakers: Jeff Richards, Managing Director at GGV Capital and Tiffany Luck, Partner at GGV Capital

Workshop Wednesdays is new series where we’ll be bringing some of the best SaaStr speakers to you LIVE, every Wednesday. 

Each workshop will be hosted in a live, interactive 30-minute format at 10am Pacific each and every Wednesday. This workshop will be 100% LIVE, not pre-recorded, and will be hosted in an, interactive 30-minute format, including Q&A.

Almost buried in Facebook’s last announcement of its workforce changes was its data on in-person vs remote work.

I call it out not because it’s a profound insight, but because Facebook is actually speaking with data, and it’s confirming what most of us think.

That at least when you start, working in the office with colleagues helps you learn and perform better.

And being at least partially in-person after that (3 days for them) showed higher performance.

I’m not reading too much either way here, and Facebook is a far bigger and more established company than any of us are running.

This edition of the SaaStr Daily is sponsored in part by LARK

Lark is a collaboration tool designed to improve team productivity. Get chat, email, video conferencing, calendar, and docs together in one place.

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