10 Key Rules to Scale Sales

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This session is titled 10 Key Rules to Scale Sales by Kris Duggan, CEO of BetterWorks.


#1 – Decide what kind of company you are

Are you free to paid? Do you work with small business? Do you work with mid to enterprise?

Make sure that you are playing to your strengths. It helps to have empathy for the types of organizations that you are working with. My past experience working at Cisco Webex and starting Badgeville has helped me develop empathy for the challenges in enterprise.

When I started Betterworks, I thought that I would focus on businesses that were 500+ people up. I found that I was pulled up market fast. We focus on selling up into the enterprise space and that’s our focus.

#2 – Target your initial customers

As a general rule, we’ve found that it takes 100 outreaches to get 10 conversations to get 1 deal. Our first 10 customers came from 10 different sources. We obtained customers from email, LinkedIn, conferences, referrals, and social. I had to go out and target customers where they were at.

One key learning that I have had at Betterworks is that your CEO has to do your sales early on. Don’t rely on a hired gun to get your first 10 sales. As you start to scale and gain some repeatability, you can start to bring in more salespeople.

#3 – Always be listening and tuning your message

When you get started with sales, you need to iterate your messaging and work on improving it by listening. The first pitches that many salespeople use have lots of jargon. Don’t fill your pitches with jargon. Speak plainly.

I recommend using what I call the Grandma test, aka the 2 beer test. How would you explain what you do to your Grandma?

A lot of times, I hear people give a pitch and then follow-up by saying “What we really do is __________.” Rather then having a really complicated pitch, say what it is you actually do.

At Betterworks, we started with “Fitbit for work,” and we’re now “Enterprise goals platform.” It’s clear, and explains exactly what we do.

#4 Scaling requires inbound leads

It takes a lot of effort to spin up your content marketing machine to obtain inbound leads. You need to have blogging, social, PR, Newsletter, Nurturing, Whitepaper, eBooks, etc. We focused on developing thought leadership and providing original thinking in the space.

It took us a year to launch and we just had a landing page during this time. We got approximately 15 leads per day. Now that we’ve launched, we have 100 leads per day. Focus on building up this inbound content engine early on.

#5 Scaling requires outbound sales

There is a lot of latent demand out there for better solutions. In order to be successful with outbound sales, you need to tighten up your target market definition. By tightening up your target market, you will be able to develop better personas to contact.

I think of my phone as an ATM. I know that outbound reps can turn 10 numbers into dollars. There is so much opportunity out there.

Remember – with inbound leads, businesses already know that they have a problem and they want to know why they should choose you. With outbound leads, you need to identify that there is an issue and then transition to why you’re the best solution for them.

At Betterworks, we started our outbound sales with two reps.

#6 Figure out the pricing

Early on, I hear a lot of entrepreneurs jumping too quickly to a pricing model. If you haven’t come up with a pricing model, a better question to ask your prospects is “How much would ______ be worth to someone like you?” Keep it simple and always charge something.

Overtime, master the elements: per user fees, commitment term, volume tiers, payment terms, and services.

Our experience – $15 per user per month, now $20 per user per month. Anchor to a comparable service if you can.

#7 Invest in customer success

Invest early on in customer success. This will help you to drive word of mouth, referrals, etc. Additionally, it enables you to be able to create case studies and get references. Finally, it ensures that you can get renewals, upsell, and cross-sell. We care about this so much that we have one of our co-founders focus solely on customer success

#8 Takes a lot of work

You’re creating something from nothing with a startup. Remember that practice makes perfect. This is going to take sheer effort in order to become successful.

#9 Focus on customers, and you end up getting investors too

“Ask for money, get advice. Ask for advice, get money.” We spend 10x more time on customers then we do on investors.

#10 Goals and Metrics

Make sure that you have specific measurements for your sales progress. You want to get your startup to operational excellence and getting better all the time. Our 5 goals are focused around the following:

  • Bookings $

  • Pipeline Creation $

  • Quarterly Program

  • Top 20 Targets

  • # of Meetings Target