How to Build a Winning Sales Team For Your SaaS Business

The desire to win is nothing without action. 

In his book, The Dichotomy of Leadership, Jocko Willink says, “What does it take to win? Yes, you have to be determined. Yes, you have to be driven. Yes, you must have the unconquerable will to win. But to really win, to truly win at all cost, requires more flexibility, more creativity, more adaptability, more compromise, and more humility than most people ever realize. That is what it takes to win.”

If you want to build a winning sales team, it’s going to take hard work and lots of action. It’ll take everything Jocko outlined and then some. Yet, it’s 100% doable, and here are some tips that’ll help you kickstart the process:

Start With Leadership

The SaaS market has more than doubled since 2015 and shows no signs of slowing. With such a tremendous leap in growth, it’s no surprise that experienced leaders are hard to come by in emerging markets. 

Good leadership is crucial to building a winning sales team. The right leader keeps the team engaged and ready for anything. The responsibilities of a sales leader include but are not limited to:

• Coaching underperformers, challenging top performers, and continually raising the bar
• Accepting responsibility for their team’s faults and shortcomings
• Remaining approachable and open to new ideas from all levels of the organization
• Getting their hands dirty when the job requires it and not feeling above any task
• Checking their ego at the door and acting with humility to accomplish the mission
• Simplifying what’s complex and clear up what’s confusing
• Providing their teams with everything they need to be successful

Most importantly, great leaders explain the company’s strategic vision and inspire junior leaders and sales reps to do more. They bring a sense of relentlessness to the office. If everyone from the newest BDR all the way to the sales managers understands the overall mission and vision, your chances of success improve significantly.

On the other hand, if sales reps or leaders aren’t bought into your sales strategy, tactics, or the way you do things, then they’ll resist change and not give their full effort. A winning sales team starts and ends with great leaders, and that can’t be stressed enough.

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Hire Selectively

Your team is already overwhelmed with their workload, and somebody just put in their notice. That’s a tough spot. Your first thought might be, “we need to fill this role yesterday!” 

That type of response makes perfect sense in the moment, but rushing the hiring process will likely do more harm than good. Throwing people at a problem may work in retail or manufacturing to some extent, but at a SaaS company, you can’t afford to bring in someone who is not a cultural fit. Being selective in your hiring process pays off in the long run.

On the other hand, it’s cruel and unusual to continue to let underperforming reps stick around for too long. It’s downright awkward to keep giving them the same negative feedback week-after-week or month-after-month.

Letting them go so that they can find a position that fits their strength is the right thing to do. Plus, it shows your team that you’re going to hold them accountable and ensure that each man or woman by their side works hard, is a natural fit, and deserves to be there.

If you have an attrition problem, then closing the revolving door should be your top priority. Slow down your hiring process and really vet out each candidate to make sure you’re investing time, money, and resources into training the right person. If people are leaving, ensure your HR department conducts exit interviews to get their candid feedback on what would have made them stay. 

Rinse and repeat until you have a clear understanding of what it takes to bring the best people in the door and – more importantly –  keep them.

Build the Right Systems

Your sales team is only as strong as their training and systems. If their onboarding process was detailed and challenging, then their performance will naturally rise. If it’s weak, lacks depth, or creates more questions than answers, you’re not going to see the value on your people as quickly.

Yet, it doesn’t stop at onboarding. Ongoing training is the backbone of a thriving sales organization. SalesForce research found that 80% of high-performing sales teams rate their sales training as very good or outstanding. 

Ongoing training could mean building your own internal mentorship program or training plan. It could also mean hiring guest speakers or consultants to come in and show your sales reps and leaders a few tricks of the trade. 

Lastly, the value of seminars, webinars, and conferences can’t be underestimated. These events give you the latest insights across the industry, help you connect with like-minded people, and challenge you in a way that books or internal training won’t.

Proper sales enablement provides the sales team with the tools, knowledge, and support they need to be successful. That means creating content for each stage of the buyer’s journey, offloading time-consuming admin work, and uniting sales and marketing teams to increase the quality of leads.

Create a Culture of Accountability

If you hire the right people, then accountability shouldn’t be a major problem. Yet, if you take your eye off it for too long, you’ll find that people’s standards begin to lax.

A big part of creating a culture of accountability is in the day-to-day interactions. Most people don’t respond well to being micromanaged, so taking a servant leadership approach is preferable. One where you’re constantly checking in on people and encouraging them to do their best work by offering help or feedback versus telling them what to do. 

Building a culture of accountability also requires open communication between reps and leaders. That means checking up on people, being responsive via Slack or email, and creating an open-door policy. Knowing your leaders are approachable and actually work hard on your behalf is inspiring and doesn’t go unnoticed.

It’s also worth noting that as a leader, you have a finite amount of leadership capital. If you spend all your time harping on the little things, people will take you less seriously when you ask them to do the big important things. 

One way to build capital is by asking for feedback and really listening. Swallowing your pride and being open to criticism lowers people’s defenses and opens them up to accept your feedback.

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Leverage the Best Technology

Much like creating the right processes or systems, having the right technology can make a huge difference in your sales team’s effectiveness. The wrong technology can slow your team down, create unnecessary administrative tasks, and even prevent them from doing their jobs if it’s constantly failing or requires IT intervention to work.

On the other hand, having the right technology can liberate your sales team from the burdensome tasks that keep them off the phones or from sending emails where they do their best work. 

For example, if sales reps were sending a dozen emails per day and manually marking all of them in your CRM, they’d be less effective than if they used a service like Mailshake to send multiple dozen if not hundreds of emails per day and have it automatically attached to contact profiles in your CRM of choice. 

The same thing goes for the checkout process. If you’re piecing together multiple sales software solutions to get customers through the checkout process, manage subscriptions, and handle all your reporting, then your sales support team will likely be bogged down in unnecessary admin work. 

They’ll likely miss out on key insights from a lack of comprehensive data and complete reporting. A solution like PayKickstart could automate the whole process and tie it together in one software.

Laying the First Brick

You’ve likely heard the saying, “Rome wasn’t built in a day.” Which is absolutely true, but you’d better believe they were laying bricks every hour. That has to be your mindset if you want to build a magnificent sales team for your SaaS business. While building a winning sales team overnight isn’t likely, doing something every day adds up fast.

To get started, take a hard look at your leadership before you begin to pass the blame to underperforming reps. The right leaders make all the difference. Next, slow down your hiring process and speed up the rate at which you put people on performance plans. It’s no longer an option to employ underperforming reps.

Finally, create a culture full of accountability by providing adequate training, procedures, and technology. Eliminate all excuses for not hitting your ambitious goals and empower your people to do their best work. 

Sujan Patel

Sujan Patel is a partner at Ramp Ventures & co-founder of Mailshake. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.

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