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  • Writer's pictureSteve Johnson

10 Top Tips to Building Out Sales at Your Enterprise Software SaaS

Every Founder and CEO faces challenges growing their companies. They’re often overwhelmed and unclear about how to navigate the growth path. They want to be certain and clear about how to gain control of their sales growth and increase revenues in a scalable and predictable way.

Here are 10 key tips to consider when building out enterprise sales for SaaS software and services.

1 – Product-Market Fit

The most common scenario I run into is a Founder/CEO whose company has either experienced some sales initial success, or they’ve been around for a while, but sales growth has been flat or very slowly trending upward.

Deals often take a lot of effort to close and their sales cycles are loooooong.

When the product-market fit is good customers will pull you into their business.

Customers won’t need to be convinced that need you. It’s much easier to sell your solutions when customers are pulling you in instead of you working hard to convince them to buy.

If customers aren’t pulling you into their business keep working on Product-Market fit.

2 – Don't Sell Tools, Solve Business Problems

I don’t agree with most legacy sales wisdom but one nugget that I believe is true is that people don’t buy drills, they buy holes.

Enterprises can be approached top-down or bottom-up. The bottom-up strategy is used effectively by companies such as Slack, at least in the beginning, by offering a low-cost solution to individuals or groups who then drive adoption throughout the company.

Many enterprise solutions don’t fit this model, especially for core operational software like inventory or data solutions which means some form of the top-down approach is required.

In enterprise sales, people buy outcomes. Enterprises buy solutions to make business problems go away.

If you want to win more deals faster stop making and selling tools that solve technical problems and build solutions to business problems.

Is Zoom just a video conference solution or does it enable businesses to increase revenues and reduce costs without requiring people to be in the same place?

Business problems are a huge lever. If the problem is big enough it creates awareness, motivation, and urgency for your customers to decide which you can use to shorten the sales cycle.

The other great thing about business problems is the people who need them solved can create the budget. Often the people who buy business tools need approval from other people in the organization. Not always, but often, people in companies who buy business solutions have the authority to create the budgets they need to get things done.

The best solutions to business problems that have a storyline that ties the outcome of solving the problem to what could be one of the top 2-3 company initiatives.

When your solution is tied to achieving a company’s most important initiatives the CEO will be on your side and interested in the success of your solution.

With your customer CEO on your side, your deals will move faster, and your close rates will go up!

3 – Customers Buy for Their Reasons, Not Yours

One of the most effective ways to grow sales is to both see your customers' issues from their perspective and talk to them about their issues from their perspective, not yours.

This is one of the most difficult things most of us will ever have to do but if you can figure it out and stick with it until you get there it’s powerful and the effects at times can seem almost magical.

Why is this?

Enterprise buying decisions are made by people, not the “Enterprise”. As people, we’re all stuck in our heads thinking mostly about the problems in their personal and professional lives.

People pay attention to their own personal, professional, and company problems that need to be solved.

Spend your time, energy, and money helping your customers solve THEIR problems and they’ll pull you into their deals and stay engaged.

4 – Personas

Finding and winning new customers is largely about presenting:

The right messages . . .

To the right people . . .

At the right time.

The right messages are about the top 2-3 key business problems you solve the outcomes for the business when you’ve solved them.

The right people are the ones who care or are impacted directly by the business problem, can CREATE the budget to solve the problem, and have either the political savvy or authority or both, to put your solution into play and ultimately get it implemented.

The right time is when they’re feeling the impact from the problem or better you’ve made them aware of potential issues and are saving them from the consequences of not solving the problem.

How do you create customer personas?

The “best” way is to talk to your prospective and current customers and identify their problems and understand their decision processes. Whole books have been written about this.

The quick and dirty way to start getting traction around personas if you have existing customers is to interview members of your team about what’s common about the customers who have had-

-the fastest closing deals,

-the deals that have been easiest to close, and

-who your best, most profitable customers are.

Typically, your ideal customers fit into all three of these categories. Target more prospective customers like this.

Make sure the people represented by your personas need to have their problems solved and have the power to make the changes to solve them.

5 – Sales Plan

Your sales plan is a tool that serves two primary purposes.

1-Resource planning.

2-A sanity-check to make sure your sales goals have a high confidence interval of being attainable.

If your company is very early stage and has limited data on sales and conversion rates the best you can do is to use this template for scenario planning and refine it often as you learn more.

Here is a simple format to get started. (For a planning template contact me and I’ll send you one to get started).

Create a spreadsheet or table with a 4x4 grid.

Each column represents one of the next 4 quarters (Q1, Q2, etc.)

The rows are for Sales, Leads Needed, FTE/Headcount, and Cash Needed.

Start with your sales goal 4 quarters from now.

Then ask yourself, “What would have to be true?” for sales, leads needed, FTE, and Cash for each of the three prior quarters.

Then ask yourself, “Given where we are today, is this realistic? y/n?”

Keep working on your plan until it matches your resources and you’re reasonably confident that you can make your number.

In my experience, it’s a waste of time to work on a more detailed plan until you’ve got the big picture nailed down.

6 – Sales Process

Once you know your customer's problems and who has the authority to buy your solutions, you can begin to document and refine your sales process.

The goal of a sales process is to make success knowable and repeatable.

Ideally, your sales process will become clear and be documented.

After a period of discovery, there should never be any mystery about what to, send, or say at every step of the sales process.

Sales processes typically are linear while most customer decision processes at best meander and at worst are convoluted.

Because of this the best sales processes are documented in a playbook and structured as a framework of taking points, both the customers and yours, sample emails, and call plans to advance deals at each step of the way.

The sales process mistake I see is that sales processes are designed around common templates in CRM systems (looking at you SalesForce) instead of your buyer’s decision process.

This leads to a lot of confusion and low confidence in pipeline forecasts.

It doesn’t make a lot of sense to make a deal at say 80% certainty because you’ve sent the buyer a contract when buyers require contracts as part of their discovery process.

This difference between reporting requirements and how customers make decisions result in a lot of unnecessary guesswork to forecast pipelines, sales, and cash flow.

There is a lot to unpack here which we’ll do in future posts.

For now, the key takeaway here is to understand how your buyer makes decisions, identify how you can help them make a better decision, and map your sales process accordingly.

7 – Systems

You need strong systems for two reasons.



You need to know if the decisions and actions you and your team are making and taking are effective or counterproductive.

You can use data about close rates and sales cycle times have broken down by deal type and sales stage to help your salespeople get better and make more money for them and you.

Sales is an expensive resource with a potentially high return on your investment. Providing tools that will make your salespeople more efficient with the proper training and accountability to use them will increase their production and satisfaction.

Sales tools properly applied makes salespeople more efficient.

Sales is an expensive human capital resource. Your salespeople are your business partners. Think of them as individual co-CEOs with you in your responsibility to generate revenue.

Maximize their efficiency.

Treat salespeople like the co-CEOs they are and expect results – that’s what they should have signed up for.

8 – Hire the Right People

Who are the right people to hire as salespeople?

Here is a shortlist to get you started.

Good salespeople-

Speak to customer problems

Help customers solve problems

Help solve more problems for your sales team and company than they create.

They have the integrity to win good deals that Customer Success can turn into successful customers.

Are assertive.

Are consistent.

(Too many organizations tolerate poor deals from sales that create a tax on the rest of the organization that crowds out quality customers. Let your competitors work with difficult customers unless you have a strategic reason to do otherwise.)

In my experience, technical CEOs and founders have the potential to be the best salespeople in their companies because they understand their customer's problems.

Often these technical leaders are intimidated by or don’t understand sales and see that as a barrier to leading sales and the sales team.

If you can build the product and get to product-market fit, you can lead sales until the time is right to hire the right sales leader.

You can do it and accountability is the key.

9 – Accountability

Accountability is simply the expectation that people are responsible to answer for their actions.

The four keys of accountability are-

1-Crisp Expectations



4-Accountability & Coaching

Every company has some measure of each of these keys but when they are crisp and working together you and your team can create significant movement in a very short time.

Crisp Expectations

Crisp expectations what needs to be done and why.

These can be defined by leading and diagnostic or reporting indicators, OKR’s or other measurement principles.

Useful dislogistic or reporting indicators for members of the sales team typically are % of quota attainment, close rates, and sales cycle days.

The quota number answers the question “Is this person producing? y/n?”

Quota, close rates and sales cycle days used together are the starting point for diagnosing sales performance issues and prioritizing areas of an individual’s sales skills improvement.

Leading indicators answer the question “Will this person make quota in the future? y/n?”.

Useful leading indicators are deals in the pipeline, assuming the deals in the pipeline are real (future post topic), and two activity-based metrics like calls made, meetings held, etc. These will depend upon your offering and what activities correlate with sales success.


You need to have the systems in place to be able to capture and report on these key, crisp expectations.

Consider bringing in a sales operations role or functions as early as possible to help with measurement.

Validate that your metrics are working and driving desired behaviors then make them public. Put them on a board or screen in a highly trafficked area.

It makes it more difficult for people who aren’t performing to make excuses, point out early who needs help and has the side effect of aligning the entire company around the success of the sales team which can have positive follow-on effects.


Cadence is regular touchpoints to review results and coach for improved performance.

In addition to publicly posting individual and team performance metrics, I suggest a weekly sales meeting, a weekly 1-on-1 deal and account planning meeting and progress on the salespersons key training focus, and a monthly 1-on-1 meeting to identify the ONE thing that, if addressed, would improve that salesperson’s performance.

Accountability & Coaching

When it comes to individual team members, the most effective sales leaders have one primary focus, to help each individual on their team improve their game to sell more and exceed their quota.

The two most important things to helping salespeople improve their ability to sell and close rates are-

1-Keep them focused only on what’s real vs what they think might be happening with their deals.

2-Keep them accountable for their skill development and sales results.

The key principle to achieve 1 & 2 is to consider what people are telling you versus what they are doing. This goes for employees as well as prospective customers.

For example, when a prospect and a salesperson are both excited because your salesperson has sent a contract over, but you haven’t completed discovery and you don’t understand their decision process, ask your salesperson “How can we quote this engagement when the customer doesn’t understand what the problem is?”

Then as they trip over themselves coach them on how to ask for what you need to provide a precise quote.

10 – Execution

At the end of the day, the things that get done are the only things that matter.

In the end, there is only what works and what doesn’t.

Don’t get too hung up on theory, academic ideas, or overthinking sales (leave that to me).

Here are a few thoughts on execution.

1-Make a plan and prioritize it. Ask yourself, what the one thing that, if implemented, would have the greatest impact?

2-Introduce only ONE improvement or significant change to your sales process or team every 2-4 weeks.

3-Test. Collect data on the results. Adjust as needed.

4-Follow through. Do what you say you’re going to do.

5-Rise and repeat.

Consistency is key. Steady progress for 3 or 4 quarters will result in 5-7 significant changes to your sales team, processes, and systems.

Do these things and your sales will grow and you, your company, and your customers will enjoy the benefits.

Please share your thoughts on these Top 10 Key in the comments below.

Wishing you the best in your sales and growth adventure!

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