10 Expert Tips for Scaling Your Startup Sales Team

June 17, 2015

If there’s one constant in sales it’s that it’s constantly changing. While the core concepts and principles may stay the same, new tactics and innovative solutions for driving pipeline and closing more deals are cropping up all the time. As sales leaders, it’s our role to embrace the fundamentals while also staying nimble and agile enough to adapt to, adopt, and capitalize on new opportunities.

That said, it’s easy to get overwhelmed by the sheer volume of new information and options out there geared toward salespeople. Luckily for you, Gabe Luna-Ostaseski, founder of Upshift Partners has teamed up with some of our favorite sales experts to produce a fantastic resource that brings together some of the best advice and latest thinking in one place. The Top 59 Tips for Scaling Startup Sales is certainly worth checking out, and I’m excited to have the chance to give you a sneak peek of 10 of my favorite tips from the guide below.

1) Set it up right from the beginning.

— Aaron Ross, Predictable Revenue

Have an inside sales team/role 100% dedicated to prospecting and generating opportunities to pass on to the Account Executives/closers. This is always priority #1! Plan to segment your inbound and outbound teams; don’t expect the same sales rep to do both.

2) Talk to people around you.

— Andrew Riesenfeld, VP Sales Development, Heighten

Find out what sales automation tools work for them. Go to networking functions and never eat lunch alone to find line-minded entrepreneurs; pick their brains about what processes work for them and be open to letting them pick yours.

3) Break down your sales cycle.

— David Skok, General Partner, Matrix Partners

Draw all of the steps of your process on a board and ask questions each step of the way to determine what the friction is for the consumer at each point. Ask if there is a quicker or cheaper way to do it, and how to improve your conversion rate. You will glean insights from seeing everything in a diagram that you won’t see from going through it every day.

4) Get everyone on the same page

— Navid Zolfaghari, Co-founder, Pinpoint Mobile

Standardize the language you are all using so the team can better understand each other. You may have different terminology to define each stage but essentially you should look to initiate, educate, validate, justify and close. This way if you hear a deal is in “stage two,” you can start to ask questions as to what was uncovered during the “discovery process.” It could take a while to get everyone on the same page, but stay patient.

5) Don’t rush the sales cycle.

— Aaron Ross, Predictable Revenue

Don’t give up on a prospect because they haven’t bought after a download or call or demo. Think: What is the next “juicy morsel” they would want, if you showed it to them, that would help them take another step forward? What new layers, content or products can you create that are compelling and relevant to where the prospect is in their evaluation and buying cycle? Document these and keep nurturing.

6) Hire up.

— David Skok, General Partner, Matrix Partners

Focus your energy on getting hiring right. It can be intimidating to younger entrepreneurs who haven’t been in a CEO position before to hire people that have been in roles more senior to what they have experienced themselves. Hire people that are better than you. Recruiting is one of the key skills that an entrepreneur needs to do; dedicate the time to it. This is where a business can break down is proper consideration isn’t taken from the outset.

7) Overpay and overhire.

— David Baga, Chief Business Officer, Honor

It sounds counterintuitive, but when your sales process is unproven, I recommend hiring a small team of reps that are overqualified for the job description. The very early hires need to be very entrepreneurial and excited about having the opportunity to help figure out the right recipe. This team is responsible for creating the repeatable, scalable and profitable model before you build a larger team. You’ll have thinner margins initially, but you’ll make up for it quickly when it’s time to scale.

8) Manage expectations accordingly.

— Navid Zolfaghari, Co-founder, Pinpoint Mobile

You want to get your team excited and do whatever you can to support them. I think everyone knows what over performance looks like, but not very many hve defined what underperformance looks like. Are you comfortable with a sales person that consistently performs at 90% of quota or one who can be at 150% one month and way under the next?

9) Put the work in early to setup strong measurement systems.

— Arjun Dev Arora, Co-founder at Immediately

Become a Salesforce junkie. Stay on top of their new applications and tools- anything to make it easier to get reporting, transparency and clarity around how your salespeople are performing. From there, make decisions on who to reward and who to fire.

10) Know how long it should take to make a sale.

— David Baga, Chief Business Officer, Honor

You can be selling a product that appeals to enterprise clients and takes three months to close, or you can close a sale in one day for a low-priced service that meets an immediate need. This time spent should be proportional to the value of the typical sale you make. Do your reps need to close multiple times per day, month or quarter? Evaluate each phase: build rapport, discovery, identify problems and pain points, demo your solution, explain costs, gain commitment, and finally, purchase — to see if it can be done faster.

49 Additional Tips from SaaS Sales Experts

Get more expert advice from seasoned founders by downloading Upshift’s new eBook:

Pages from Ebook- 59 Tips for Scaling Startup Sales

Photo by: Danist Soh


<strong>CeCe Bazar</strong> is an Associate on OpenView's investment team. She was previously a Sales Strategist also at OpenView.