A Founder’s Guide: Mapping Your First Sales Playbook

I want to set expectations: this is not a short blog, and it’s not meant to be. This is a 10 minute tactical guide for early-stage companies, and after that a ~5 hour project that can change the next 12 months of how some of your most critical hires work every day. In my opinion, it’s the most important thing you can give your revenue owners on their first day so that they feel confident from Day 1 to Day n. And you care about revenue, right?

Here’s where we are: things are good, your company’s product-market fit is tight, you just raised an early round of funding. Now it’s time to ramp up and hire revenue-generating team members: SDRs, AEs, CSMs, Insert-Other-Acronyms-Here. When you’re in this situation, it’s pretty exciting. It’s also the point where young companies typically lack discipline and fail to realize that the seeds they sow today in adequately onboarding and training their teams will lead to the successes (or lack-there-of) that they reap 12-18 months down the line. I get it, just like thinking of planning for retirement at age 23 years old, it’s hard to think 12-18 months down the line when your company isn’t even that old yet. This sales playbook guide from Bowery Capital’s Acceleration Team will make it easier.

Here are three critical (short term) reasons to have a sales playbook:

1. It creates uniform messaging and processes across your team. No miscommunication and no excuses.


2. It drastically decreases rep ramp up time which means more money in your pocket (and sooner).


3. It gives you a structured opportunity to collaborate together, learn, and crowdsource best-practices from across your team (even outside of sales). A sales team that shares each individual’s strengths in selling is always greater than the sum of its individual parts.

Here are some significant long-term reasons:

1. You only have one chance to make a first impression with a new hire as to the professionalism of your organization. Furthermore, early successful hires will go on to interview, train, coach, and hire others, so there’s a multiplying factor here.


2. Sales orgs already experience massive turnover. This reduces it.


3. Compound interest (of sorts). The quicker your rep covers their own cost, the quicker they become cash flow positive, which can result in a lower burn rate, extended runway, greater control of your own destiny, more freedom to iterate on your product without the pressure of your board, and so on and so forth. You literally experience increasing benefits over time by ramping up, onboarding, and continually arming your sales team to perform better. As Eric Schmidt has famously stated many times, “Revenue solves all problems,” and that starts with preparing your revenue generating team.

So what’s the actual structure and technique for our first playbook? Below is a simple outline we train all our early founders at Bowery on as a starter pack.

Buyer Personas We Sell To

An outline to help your sales reps more quickly identify your ”Ideal Contact Person” (ICP) at companies you sell into. This should include what the company itself looks like (# of employees, revenue they generate, location?), the individual’s title(s), compelling reasons they typically buy, and features of your product they value highly. Rinse and repeat for different personas within the org.

Outbound Email Strategy

If you’re not already measuring the best email templates or calls you use for outbound, you should! This is also a great chance to poll the whole team and figure out what works best. You can then include those templates here.

Discovery Question Examples

What should your reps be asking to understand who they’re talking to better, and ensure they’re ready to buy? Maybe even more important, what should they be asking to decide they’re not ready to buy, so you can move on? Some people swear by the BANT framework here, while others rely on SPIN selling, and so on. Whatever the acronym may be, you should figure out, test, and arm your hires with frameworks of discovery questions.

Sales Script

What this is: a written script of how the perfect demo would be laid out. What it is not: the reality of how your demo will actually come out. Huh? What I mean is, every demo should be slightly different and tailored to your prospect. You should almost never cover every single feature of your product. That said, this serves to educate people internally on the order of operation, value propositions, and closing statements within an ideal, all-inclusive demo.

Customer Objections & Answers

Crowdsource crowdsource crowdsource. Discuss this with your team and take their combined years worth of knowledge around your months-old company, and identify the biggest objections customers have and the best answers you can collectively come up with.

Competitive Analysis

This is an ongoing battle, but one that should still be revisited and fought regularly. I always suggest you sit as a team for 30 minutes every quarter to discuss your competitors, what you know about them, their pricing, and successful messaging you’re using to overcome the distraction that competitors bring to your table.

Pricing & Negotiation

How many times have you heard managers having problems with their salespeople “going rogue” and offering discounts here, or special services there, that aren’t approved? Alternatively, how many times have you seen “Sales Rep A” give “Sales Rep B” the hairy eye because B is employing a pricing and negotiation tactic successfully that A didn’t know they had at their disposal? Well, that stops here. For more info, I love John Barrows’ give-get negotiation for building a framework and Price Intelligently’s Value Metric Blogs for how to establish pricing to begin with. Furthermore, revisit pricing quarterly too to make sure it’s working well.

Sales Funnel Outline & How to Use our CRM/Sales Tools

Let’s face it, your sales ops person (or whoever owns this duty) is always going to feel a bit like an enforcer chasing people down to use the CRM correctly. I don’t know a single early-stage company that has this pinned down. With that said, if you lay out the rules of the road as to how your CRM works, what your sales funnel looks like, and when things are allowed to advance from one stage to another, then you at least have some accountability here when chasing people to do things the right way. Furthermore, I can’t stress enough how much of a treasure trove of data your CRM is, especially early on when you have fewer customers and you’re scrambling for data points to understand what works. Everyone needs to participate here, and that starts with clearer instructions.

Finally, your new hire should receive your playbook on Day 1, and then there are some critical steps after this. First, a sales-specific onboarding schedule should be designed (on top of general onboarding), which closely mirrors training each of these sections. Next, you need some sort of accountability. Some organizations make their new hires sign this doc, and employ tests to ensure the new sales team member knows these things cold and is “certified” to sell. On the flip side, the training team needs to be held accountable too. Having your new employee fill out a feedback form later on, or rank the onboarding sessions with commentary on how useful each session was ensures this, and keeps you in the mode of improving. We’ll get more into what to arm your sales team with after their first day in future posts, but for now, hopefully you feel ready to throw your new hires into the mix, ramp up, and take off!

If you liked our Sales Playbook and want more sales-related tips and content, check out other relevant blog posts from the Bowery Capital Blog.