Sales Organization Structure: How to Scale Your Sales Team

What to Expect as You Scale #

Before we get into how you scale your sales organization structure, it’s important to be prepared for what the process of scaling feels like. It can be a rocky road, to the point of making you feel like you’re being punished for your success.

First off, your market will seem more crowded with elite competitors. Your product offering will likely have diversified on your way to scale-up level, meaning you’re competing on more fronts with more companies. Your benchmarks — for revenue, churn rate, and customer lifetime value — will have changed accordingly, and you’ll need to adapt to the pace of your new competitors.

Speaking of diversifying your product offering — your product will also have become more complex during scale-up, and it will likely continue to become broader and broader. Your sales team will have been accustomed to selling it as a narrower collection of features. However, as you add more features for new personas or verticals, your sales team will have to get used to selling your product in different ways.

You’ll also find as you scale that marketing becomes more demanding. During scaling, your sales method inevitably takes on more passive elements (e.g., more responsibility to things like content marketing, video series, and online seminars) as marketing takes more responsibility for drawing in new customers. Your sales team will be tasked with adopting your marketing department’s messaging framework.

As you scale and look to strike bigger and bigger deals, sales cycles will become more complex, requiring deeper documentation and technical assurances. This becomes particularly true if you adapt your sales organization structure for a higher volume of enterprise sales. Enterprise sales, also known as complex sales, involve vastly larger contracts and often come about when you’re selling to an entire company; in return for providing massive revenue boosts, enterprise sales are higher risk and involve longer cycles.

And finally, scale-up time is usually the time when all your cunning technical shortcuts and makeshift solutions cease to be as useful. As you hire RevOps and sales enablement, they may well inform you that you need to update your tools, patch up your UX, fix those lingering bugs, and even re-platform.

5 Tips for Scaling Your Sales Team #

Scaling your sales organization structure means responding to challenges in a sensible and systematic way. To have arrived at the point of scale-up means that you’ll already have a stable revenue base, a monetization strategy, and at least a handful of sales processes that work. The trick now is finding ways of making what has already worked for your sales team work just as well at this level.

1. When and Where (Don’t Rush It!) #

Knowing how to scale your sales team and sales organization structure is all about timing. Broadly speaking, then, you’re ready to scale if your leads are in plentiful supply, your benchmarks are secure or, you have high sales maturity. In the words of Joe Caprio, Chorus’ VP of Sales, scaling is “truly a question of crawl, walk, run”.

Young startups are often confronted with a great problem: A lot of funding, very quickly. You must balance ambition with practicality so that you end up with a stable, scalable business.

How do you know if you’re ready? Begin by assessing every aspect of your sales organization structure to find out how prepared they currently are for scaling.

For example, let’s say you’re a company that tracks time-on-the-job for employee bodies. If your sales strategy has generally been made of wide-net methods of approach — email newsletters, content strategy — then there’s a strong chance that you’ll have overlap in the audience you’re reaching. In other words, you can’t be sure exactly how broad the size of your prospective customer base is or what industries that base is centered in.

This kind of company may not be ready to scale. Your audience needs to be big enough and diverse enough, and you must have a precise idea of how big and how diverse, in order for it to supply the quantity of leads required to sustain a scale-up.

Likewise, if your quantity or quality of leads tends to fluctuate, then your process for qualifying them needs to be improved before you can sustain scale. Scale is a question of quantity: if you cannot depend on a consistent supply of leads in the sales funnel, then you cannot afford to scale.

For example, let’s say you’re a company that provides a cutting-edge LMS platform to other tech companies. Your product itself may be of the quality needed to sustain your business at scale, but your business development team is not sufficiently well built or directed such that you have a steady but not excessive lead backlog every month. Your sales department are hitting their targets too easily, and finishing the month with barely any leads to pursue. This kind of situation is indicative of a company not quite ready to scale yet.

The main point: Just because you’re not able to scale right away, doesn’t mean that you shouldn’t be preparing to scale, and making moves accordingly.

Preparing to scale should inform your hiring strategy - and when it comes to hiring, proactivity is key.

Focus on bringing in force multipliers, like RevOps and Sales Enablement, with your Series A - don’t wait for further investment to come through first. Joe’s philosophy on this is to "Act like you’re 6-12 months ahead. Don't wait to make investments to support your team's scalability."

2. Know What You Need #

You’ll be making different kinds of changes to your sales organization structure based on what kind of scaling/expansion you’re looking to accomplish. Knowing the direction you want to scale in makes new hires and restructures easier.

If you’re expanding to an office in a new geographical territory — perhaps the most extensive type of scaling — you need to consider a host of practical issues alongside any structural changes. Thanks to the nature of SaaS -- replicating tech stack set-ups, etc. -- shouldn't be a problem, but you will have to consider office space and other overheads. On top of that, you'll have to think about the recruitment pool in your new territory: will there be enough of the types of specialists you'll need to build a new sales team there?

If you’re trying to scale-up in the pure number of accounts with similar verticals, your sales organization will need more account managers/reps and potentially more sales supervisors to oversee the expansion. You may wish to hire specialist account managers in order to give your reps more time to sustain the volume of selling needed at scale-up. Because this kind of scale-up involves trying to establish a larger share in your original market, you may also wish to bring more marketers into your sales organization structure.

If you’re trying to scale-up the number of industries/verticals you serve, then your sales organization structure may need to accommodate a broader range of new faces. You may need to hire more devs in order to develop a more complex product offering suited to the new industries. New business reps may be required to broker deals, and promotions supervisors may be needed to oversee aggressive marketing drives into the new areas.

Knowing what you need also extends to knowing what targets you need to be hitting on separate metrics. In Joe’s words, "The most common exercise we go through in scaling sales orgs is identifying what we need to hit on which metrics. Do we have an actual, month over month plan to track progress towards goals? Are we reviewing the assumptions along the way."

3. Make Sure Your Tech Stack and Sales Processes Are Ready #

You can more effectively scale your sales org structure by implementing your strategy before you scale. That’s especially true when you’re talking about tech, tools, and fundamental sales processes.

Joe recommends: "Ensuring that your process is fluid and enabled by the right tech stack is critical to building a high functioning, high growth sales org.”

Your first priority is to make sure your sales process is standardized and robust. To do so, gather data on your sales process to drive your time-allocation decisions, and make sure that your sense of your buyer personas is well road-tested. Every part of your process should track back to an understanding of those persona types. Without them, your sales funnel won’t be able to supply you with enough high-quality leads after scaling.

Your objective here is to come up with a sales process that is easy for all of your reps to replicate. You can’t keep track of endless varieties of approach at scale, so find the method that works best, and get your whole sales organization structure on board with it.

Data is your best friend during scale-up. Track and forecast data from your sales processes relentlessly for later ease of optimization. Some of the most important process-related data to collect will concern things like the following:

• What methods are you using to approach your prospects, and which ones are working? Are you having a lot more luck through social media targeting than through cold-calling? Is your content marketing over- or underperforming relative to conversions?
• Are you seeing the LTV predicted from the buyer personas you’re targeting? If not, it may be a sign that your price points are too low, your customer acquisition costs are too high, or your churn is too high.
• What kind of responses are you getting from your customers during the free-trial period? Is there a spike in interest during the trial, or a loss of it?
• How are you setting up price points? Do you know what your most popular features are and what your customer base’s average willingness-to-pay is relative to those features?

Your tech stack will have played a key role in getting you to the point of being ready to scale. If you need to change to a more scale-friendly or easy-to-use CRM system or invest in a bunch of new accounting software, do it before expanding. Re-platforming is considerably easier with a sales team of 20 than with one that has 80 members across three offices — it’s a good idea to get RevOps and sales enablement hired early during scale-up\to avoid these kinds of stumbling blocks.

Likewise, sales enablement technologies like Conversation Intelligence are most useful when their deployment has been prepared for pre-scale. Having the right solutions in place in advance can mean your sales team flies out of the blocks after scale instead of needing six months to find their feet again

Your approach to buying new tech is also a good barometer of your business’ maturity. It’s as Joe says, “you can't buy tech without a clear business case and corresponding ROI calculator.”

When you’re seeking new technologies for scale-up, don’t treat your vendors as an opponent to be bested. Talk honestly with them to find out how they can best support you. As Joe observes, “Too many companies buy something off the demo and "let it fly" where they just wait for organic adoption and outcomes to follow. Get specific with your vendor and your users to ensure everyone is aligned on exactly how this particular project drives revenue/cuts costs etc.”

4. Settle on How You Coach #

Standardize your coaching curriculum, particularly during onboarding. While there may be scope for acclimatized sales reps to be coached on individual challenges, bring new reps into your sales team with the same onboarding process. Be comprehensive during early training. Companies likeHubSpot get new hires to generate a blog about their experience with the product, giving them a unique insight into the feelings of the buyers they’ll be selling to.

Embrace learning management systems as part of your structured coaching. They can help keep coaching happening at a steady and non-disruptive pace while giving you license to throw new reps into action earlier.

As with your tech stack, plan ahead. Implement two or three coaching programs before you scale to ensure that your coaching methods are standardized across your sales team. Scaling your sales organization structure requires a sharing of sales burden through your team. The longer you leave a few all-star sellers to drive the lion’s share of your revenue, the more difficult it will be to get the rest up to speed and maintain consistent growth when the market grows more competitive.

5. Know What to Look for in Each Hire #

The make-or-break element of scaling your sales organization structure is who you bring in. To make the right decisions and hire the right people to make your scale a success, you need a process.

You’ll find recruitment very time-consuming and scaling highly unpredictable if you can’t build a solid picture of your ideal hire for each new role. This is true of whatever position you’re looking to fill.

Metrics and quantitative approaches to process-building often have a payoff wherever they’re used in sales, but they really pay rich dividends when you’re trying to scale. That’s especially the case when you’re trying to build a clear, repeatable picture of what kind of personality profile best suits your sales organization structure. Build up a predictive index, made of key criteria for what a successful salesperson looks like for you, unique to your company and product.

For example, you may find when hiring sales reps that you have a team currently rich in competitive, tenacious personalities. To make the profile of that team more versatile, you may then wish to introduce new reps that bring those qualities while demonstrating the social intelligence needed for SaaS sales. If your new reps are more likely to be working across new, unfamiliar verticals, ready-to-learn reps should be your first port of call.

The same goes for adding new sales leaders to your sales organization structure. After assessing the profile of your sales team and your industry, what kinds of attributes and experience would your new sales leader need? Do they need to be able to handle a relentless pace of work and an ultra-competitive sales team? Do they need to be very coaching-oriented and capable of relating to a much broader profile of subordinates?

Use tools like Lever that assist you in matching a prospective hire’s unique sales signature and approach to your context. Do they fit with what you do and how you do it?

Scaling Never Sleeps #

The scary, exciting thing about scaling is that, once your company has started on the road, scaling never really stops. Before you know it, your company’s sales team will have grown from 15 to 30 to 90 to 200 members.

To keep a handle on it, you need to be as careful and systematic when tailoring old processes and coming up with new ones as you were innovative and spontaneous in the early days of your company. Scaling is the time for the careful reading of data, the improvement of old methods, and the injection of fresh blood. Nail the balance and you’ll be scaling well beyond the competition.