How to build and evolve your first sales playbook with Bowery Capital’s Andrew Oddo

Collin Stewart, CEO

15 August 2019

Growing a company rarely, if ever, happens fast enough. Whether you’re bootstrapped or venture-backed, the drive to close as many deals as possible (in the shortest amount of time!) is strong.

And why shouldn’t it be? More sales means more team members, more team members means an expanded product, and an expanded product means more sales. 

Establishing a solid sales process when you’re first seeing real signs of growth, however, can be a challenge. You’re going one hundred miles an hour – who has time to think about effective procedures, right? If you slow down, you’ll lose sales. 

But early-stage companies, and their small sales team, can actually save themselves a lot of hassle by slowing down and putting together a sales playbook in those early days, says Andrew Oddo, Director of Growth at Bowery Capital, on a recent edition of The Predictable Revenue Podcast.

All it takes is a working knowledge of a few core concepts: your Ideal Customer Profile and buyer persona, and your sales channels and messaging.

“I’ve helped a lot with sales playbooks. But going into my role at Bowery, I knew media tech, and a lot about ad tech, but had to learn about other spaces. The good news is that the playbook is the same – the buyer persona, qualification framework, CRM regimen, for instance,” says Oddo.

“That’s why we see really good SaaS sellers be successful across verticals. And that’s why a sales playbook is one of the first things we do with our portfolio companies. We think of their roadmap and the boxes we need to check off and get it into a digestible checklist.”

The benefits of a documented sales playbook 

So, what can a sales playbook do for your company? How can it help? For starters, it can be a north star in an often hectic (chaotic?) environment.

“The reason it is such a part of our culture at Bowery is that when you get $3 million wired to your bank account, you often aren’t ready for all of the things you need to know. But you have to stay focused,” says Oddo.

“Most people raise their Series A about 18 months after your seed round – and you need to get to about $1.5 million or $2 million to do so. The playbook will help you focus on what you need to do, as well as keep the cost of acquisition and other important costs down.”

It also helps the sales teamwork across the company: you get critical information from the product team, from finance, and from customer success to fill it. Critical information from each of those departments should always be in a sales playbook. Sales can sometimes be a siloed practice in a company – they are always on the phone, ready to deal with a prospect at the drop of a dime. By having a unified sales playbook, one with contributions from each team, it highlights the interconnectedness of the company and shows how every piece contributes to the whole.

Finally, if you want to hire a great director of sales, one way to put them at ease is the sales playbook. It’s always a risk to go to an early-stage startup, so a document like this helps them assess the maturity of your organization and that you are serious about sales.

“Of course, a seller may not make more money when joining an early-stage startup. So, you can’t just say ‘hey, you’ll make a lot of money,’” adds Oddo.

“But a sales playbook can show them that will be working on more than just the nitty-gritty and that they spread their impact in ways you can’t do at larger organizations.”

Pieces of the playbook

Despite all of the possible additions to an effective sales playbook – and the people that can contribute – a playbook doesn’t have to be a long, onerous document. In fact, it shouldn’t be: Oddo says young companies should aim for a document between 5 – 15 pages long.

And the critical concepts a playbook should include are:

  • ICP and buyer persona – this is critical. If you don’t know these answers, you will want to define them during this draft process
  • Sales channels and messaging – you might have an amazing product, and great value, but you need to nail the first 30 seconds of your pitch or you’re going nowhere. So, hone your messaging (it can, and should, always be evolved), but a solid draft of your outreach should be made available here.
  • Qualification questions – whoever your buyer is, you need to understand who is a good fit or not. Good qualification is critical.

Other important concepts that can be included, once you have the above in place: 

  • How to pitch
  • How to use your CRM
  • How to negotiate 

“I’m coming from the B2B world. It is not enough to say ‘here is every one that downloaded our app’ in a playbook,’ says Oddo.

“You need to think about your total addressable market and understand how many of a particular buyer persona is out there and understand some of their attributes.”

Of course, you can do a lot of that work ahead of time. For example, at the company level – what industry are they in? What is their revenue? Financials? Employee count? These can all be found for free and are factual pieces about the company.

At the buyer level – what is their title and seniority? What particular business unit are they a part of? How long they’ve been with the company? 

It’s important to note: these are all attributes that can be found in a database. It is important not to overload your ICP with esoteric attributes that are difficult, if not impossible to prove. Stick to the basics, and you’ll be fine.

As for your channels and messaging – this is all about reducing the time you are wasting. If you know one channel is way better than use that.

And you should know how those channels want to be communicated with – is it calls? Emails? A multi-channel strategy? And, what does your cadence look like? (Older industries like manufacturing, for example, may prefer the phone. If you’re targeting product managers in San Francisco, on the other hand, you may be better off using maybe emails).

Too many sellers give up after one touch, but sales takes determination.

Finally, have a compelling call to action documented in your playbook. This is critical. Of course, it will be iterated on regularly – but you should have some effective messaging ready for anyone who reads this document.

(Editor’s note: we had Mark Kosoglow from Outreach on the pod a while back to discuss how he empowers his team to uncover the pain points and needs of their customers. You can read about our chat here, or listen to the whole interview here)

Arming your team

What this all comes down to, adds Oddo, is arming your team with the most knowledge and confidence you can.

If you have something like this in place, you are trying to give your sellers a key to success. When you don’t do this work and you have a seller fails, then you have to put the blame on yourself and realize there is more work to do. You need to have the right systems running – so have them ready for your team.

The playbooks can change, of course, to ensure you are always as up to date as possible. 

To help with that update, assign people to do a quarterly review. For example, have a team member own each section of the playbook. This is a great chance to assign mini-leadership roles to your team and see how they respond. When someone new starts, you can have them go through and update it as well.

Ultimately, a playbook makes sales no longer a game of guessing,” says Oddo.

“So do some good research around your ICP. It will help you close and it will ensure you better conversations. Even when a prospect isn’t going to buy, this shows you’ve done your work. They, and your team will appreciate it.”

For more on Oddo’s expert tips on how to build a sales playbook, check out his full interview on The Predictable Revenue Podcast.