Hiring for Sales: Fuzzy Math and Four Letter Words…

For the most part, people don’t know when to hire for sales in digital client services.

Truthfully many people are mostly-sorta guessing when they should hire for billable roles too... But when it comes to an unbillable position like business development, man are they guessing. Frequently recurring questions I field include “When should I hire for sales, or grow my sales team?” “What signal should I listen for amid the noise of my business to tell me to hire or grow sales?” “What number on which spreadsheet shouts ‘hire!’…?”

I’ve worked with dozens of agency owners, I’ve interviewed and spoken with approximately 100–150 more, and I’ve moderated business development conference panels and conversations with hundreds more owners. Across the board there is one consistent point in time that typically triggers most owners to hire for business development. They hire way too late.

The Money Experts…

I get asked this same vein of questions (about when and why to hire for sales) from financial advisors, consultants, and CFOs who work with agencies too. Dwell on that for second, go ahead explore the space. These are advisors who make data-based recommendations to their clients that drive their budgets and their businesses, and they don’t know the answer to “When should I hire for sales, or grow my sales team?”

They’re right to acknowledge what they don’t know. The reason is their sample size is way too small. While those advisors often make recommendations about how to staff and budget a small business (based on data and experience gathered from millions of other small businesses*) the publicly available data about small digital client services businesses specifically is simply too microscopic to be truly valuable.

*This data is deeply flawed as it relates to digital client services too. Using data from millions of small businesses to determine hiring and staffing for example, assumes that hiring and staffing in digital client services behaves much the same as hiring and staffing within that larger universe of millions of small businesses. It does not. Hiring and staffing is more competitive in digital client services than it is in most other industries. As a former recruiter in digital, I worry if these financial advisors and CFOs take the unique costs of recruiting and retention for digital client services into enough consideration, or if their recommendations are noisily clouded by bad/generic data.

Soft Algebra and Fuzzy Math

My own insight is completely anecdotal, and similarly mathematically terrible. If you prefer advice substantiated by data, then this is inherently bad advice. That’s all there is to be had. I own my mathematical terribleness however. Buyer beware.

In hundreds of conversations with owners, I’ve spoken with two (2) who intentionally hired for sales in advance of their agencies’ current needs. Two owners in hundreds who had the instinct (and capital) to invest in a sales team that represented the kind of results or growth they wanted to achieve.

Previously I urged owners to Get Ahead in Sales. What I didn’t feel comfortable doing then, was putting some math behind the message. Some hard numbers and some hard metrics. What follows is some soft algebra and fuzzy math for your consideration based on my observations from the front.

TLDR Version

8–10 employees: Getting serious with a project manager. Most agencies’ first sales hire is a PM. Never underestimate the pivotal role PMs play in client services, and by extension sales.

12–18 employees: Adding a sales support or business development lead. An owner who has led sales to this point, often hires someone junior to support their efforts (sales support), or someone more senior to replace parts of their role in sales or focus on lead generation (business development lead). The owner typically remains heavily involved in sales at this point rounding out a two person sales team.

~25 employees: An additional business development lead resource is added, or a support resource if one hasn’t already been hired. This leads to a sales team of at least three, including a dedicated owner still. This new hire depends largely on the previous hires (see basketball team analogy below), but the sales team at this point typically includes sales support, a business development lead, and fairly fully committed owner/principal. This team could include two full-time business development leads, or a sales person plus a marketer, but the lead + support + owner is the most common combo.

30–35 employees: Time to build out a sales organization. At this size a more robust sales team is required. This team can include more than one business development lead, a marketing director, sales support, and account management (in addition to, or as a part of your PM structure/role). You’re building the sales organization a larger firm will need, because agencies don’t hover at 30 people for long. They either accelerate toward the next plateau around 70+ or contract.

The Long Version

12–18 employees. Most digital client services firms hire a dedicated, unbillable resource for business development when they grow to somewhere between 12–18 staff members.

Many hire for project or account management prior to that, around 8 or so staff members. These project and account managers play an important role in sales too, but we’ll put that conversation aside for a moment. Love you PMs, mean it.

This first dedicated business development hire is often either a sales support resource, or a business development lead. Let’s unpack both a bit.

Sales Support

A sales support resource typically works with a principal who still leads sales. The support resource may manage email communication and scheduling with new leads. They sometimes have a role in documentation, everything from meeting notes to proposal framing. They might have reporting and forecasting duties. If a principal imagines their time is worth $500/hour, this support resource takes on many of the responsibilities that would bill at a lower hourly rate.

A brief word of caution: This is often referred to as “PM’ing the sales process.” That’s what I called it too in a previous life. I think this description is a bit of a disservice to good PMs though, because business development is the Tyrannosaurus Rex from Jurassic Park. It eats when it wants to eat, and shits when it wants to shit. Good PMs lead, and often there isn’t a leadership opportunity for a sales support resource in business development. Most often these support resources are administrating a principal’s role in sales, not business development itself.

This is an important distinction because often when this support role is hired, the support resource is “responsible” for the cadence and progress of sales. Respect the term PM.

Ever try to push a piece of wet spaghetti across a plate? You can’t push it from behind, you have to pull from in front, sales is often a wet piece of spaghetti (as well as a hungry dinosaur). So a business development lead might be the first dedicated sales hire.

Business Development Lead

A business development lead is most often hired for one of two reasons, for lead generation, or to free a principal of their sales (burden) responsibilities.

Lead Generation

When these leads are hired for lead generation, it may be because inbound leads have slowed, or are not growing at the same pace the agency is growing. In these cases sometimes a lead is hired for lead generation because they are perceived to bring a huge rolodex of client contacts with them. Sometimes they are hired because they scream “hustle” in everything they do, and the potential volume of activity is exciting. The short version is this lead is going to apply energy into the prospective client universe, and results will follow.

A brief word of caution: This can often lead to cold calling, email blasting, drip campaigning, and other ideas that sound like something you’d use Angie’s List to fix. Worried conversations about commissions and incentive structures spring from the fear these ideas conjure. Spoiler alert: there is no right answer about commissioning or not commissioning. Every agency is unique, and every business development lead is different, and you should plan accordingly. Anyone telling you “Always commission!” or “Never commission!” is an asshole. Generally anyone making gross generalizations about any group of people is an asshole. See? I know because I’m an asshole.

Sales Leadership

When business development leads are hired to unburden a principal of their sales responsibilities, that means the agency is a year or so away from going out of business.

Just kidding! Kind of. I wanted to make sure we’re all still paying attention.

In this role replacing aspects of a principal’s role in sales, a business development lead may assume control of closing leads, writing proposals and estimating, pitching, and nurturing sales through the sales pipeline.

Two important questions to answer in this hiring scenario are “Why does the principal want to become less burdened in sales?” and “How much oversight will they still invest in sales, once a lead resource joins the team?”

If the owner wants to become less burdened in sales because they perceive someone else would be better at it, then that’s an instinct worth pursuing. That owner is likely invested in sales to such a healthy extent, they want to improve it by getting a little bit out of the way.

A brief word of caution: Don’t go too far though. NOTHING is as impactful to a prospective client as the attention and interest of an agency owner or principal. The best sales person in the world is taking a knife to a gunfight when they’re pitted up against an owner, who has taken time away from all of their many responsibilities, to engage with a prospective client in the sales process. Additionally an owner needs to be fluent in what is occurring in sales, for forecasting, for peace of mind, for the sake of their business. Don’t go too far...

If the owner wants to become less burdened because they are bored or tired of sales, then they have already decided they don’t want to own or lead a client services company any more. They may not realize it yet. Sales is half of the equation in client services, the other half is doing the work. You can’t fall out of love with half the equation and stay in business for long.

Preventative Medicine

In each of these cases, these initial hires are often being made out of sheer exhaustion. Exhaustion from the hustle of the sales process, exhaustion from the pressure of winning sales, or the exhausting of a formerly-more-robust inbound pipeline.

Business development could be (SHOULD BE!) preventative medicine, but most often it’s not. In the cases outlined here the business development hires occurred well after symptoms presented.

As digital client services agencies grow, their business development needs and requirements continue to expand. Salary, benefits, and operating costs multiply like gremlins in a hot tub.

No sooner is a sales support resource hired, then a business development lead is needed to back fill an owner who has now focused more acutely in a specific area of business development. No sooner does a business development lead get their bearings, then a support resource is needed to free them to focus where they’re appropriately billable, rather than in the weeds of administration.

~25 employees. By the time many agencies reach a staff size of around 25, there’s room in business development for some combination of an engaged principal or owner, and up to two (or three) full time resources. One or some of these parts can be played by another owner or principal, but this means coordination and scheduling is 100x harder. The mix of these roles and responsibilities varies from agency to agency.

At this size you’re composing a basketball team in sales, not a football team. I’ll explain, because I love talking about basketball.

Basketball vs Football

A basketball team is five players on the court, and a team of fifteen active players. They play in a fluid, non-stop sport where improvisation, muscle memory, and team dynamics shape outcomes. Plays build on plays, and variables are always changing. You design a good basketball team around the abilities of the five players. You find a way to orchestrate their individual greatness, into custom-crafted team greatness.

A football team is a massive seventy plus roster with eleven players from each team on the field, four times as many total compared to a basketball game. And those players stop and start before and after each play. Players discuss strategy, line up in specific set positions, execute a play, and then regroup and repeat. Due to the intensity and violence of the sport, there is a “next player up” mentality in football too, which means roles are designed. Players and their substitutes fit into those roles. When new players join, they fit into specific buckets with specific defined roles. In football you build a great system, that individuals are organized into.

30–35 employees. When you reach north of 30 staff members, you need to start getting deadly serious about building a sales organization. At this size many agencies begin to feel the irreversible gravitational pull towards growth. Beyond a team of 35 or so staff members you need a profound investment in new business, account management, marketing, and closing sales. Read Aurimas Adomavicius’ post on Building a $20 Million Sales Organization for some wayfinding into that dense wilderness.

Buying Time

So that’s a lot of observations, but I wouldn’t leave you without some advice. I wouldn’t do you like that boo.

The conclusions I’ve drawn from these numbers (math so fuzzy it sounds like a Neutral Milk Hotel single) is that generally speaking, owners and principals reluctantly and begrudgingly hire for sales. When the pain is so acute it can no longer be remedied, or the numbers on a terrifying spreadsheet are screaming so loudly they can’t be ignored, that’s when business development hiring often happens.

Each business development hire unlocks more time for business development, and that’s what most principals really need. More time. If owners could buy another 20 hours per week for them to invest personally in business development, they’d do it 99 times out of 100. But they can’t buy more time, and HR, operations, delivery, client services, and management gobble up tons of their existing time.

Hiring for business development seems like a simple solution. The reason owners and principals often delay as long as they can though, is money.

A sales support resource is a hefty unbillable investment. They are pure cost, and they can feel like a luxury when everyone in the smaller agency to this point has been blissfully billable.

A business development lead can easily be a six-figure investment, another unbillable asset, which is tough to stomach when owners are accustomed to billing for everything. If the business development lead is commissioned and really good at their job, it only gets worse. They’ll make even more money than the owner. Did you hear that in the cheap seats? If you’re paying someone on commission, their earning more than an owner means they’re good at their job. It means they’re killing it, celebrate.

So I stand by my previous, under-read and under-Medium-applauded advice, Get Ahead in Sales. But if you can’t make that huge salary or budget leap right now, how can you hop a little?

Part-time Support

You don’t need to hire someone full-time for them to materially benefit sales. Figure out what tasks you need accomplished to serve your various sales campaign goals, and Sears Catalog Wish List of strategies. Compose a bullpen of part-time resources to service those goals. Find great writers, content strategists, freelance marketers, and designers who can offer specific support in specific areas. Hire them for projects, then deploy again and again as needed. Or better yet hire them for a project and pay attention to how they do what they do. Then internalize that process with a dedicated internal resource if it’s valuable enough.

Get ready to delegate parts of sales, the parts where you are mostly replaceable. Take Richard Banfield’s advice. If someone can do what you do 70% as capably, delegate to them.

Trust me, I’ve made a living over the last two years providing fractional business development support. And I’m doing so well I have time to wax philosophical on Medium. What a big shot! There is a model for this to work and I’ve seen the results. They are much better than not doing anything. Be careful who you hire though…

Outside Service Providers

My best advice is to vet these folks like they’re a Supreme Court nominee.

For example, there are tons of lead generation services now that guarantee meetings, guarantee leads, guarantees all the way down. They appear to offer turnkey business development hustle, that requires little to no time and support from owners or principals. Seems almost too good to be true.

I have not worked with these service providers myself, but their reputations precede many of them. What worries me specifically is they offer a foolproof system, a recipe that can’t fail, and I bump against the idea that any approach is rinse and repeatable across various digital client services teams. Each digital client services organization is inherently different, especially at smaller scale. Remember the basketball team? This feels like a football solution to a basketball problem.

Get their references, on the phone. Spend time getting to know the references and their businesses. Develop an understanding of how they sell, what they sell, who they sell to, and determine if they and their business feel analogous to you and yours. Then explore the highs and lows of the outside provider’s process and results. What were the positive outcomes? Where was there friction? What bridges were burned? What friends were won and which people were influenced? These services charge thousands of dollars per month, and they’re at their most profitable when they’re charging lots of agency clients at once. It feels super transactional to me, and I don’t think there’s one bulletproof approach out there that works for everyone.

There are other promising newfangled creative solutions out there too. I won’t name drop for fear of getting labeled an advertisement by Medium’s new content policy, but do some Googling and you’ll find them. Invest wisely, ahead of your needs when possible, fractionally when you can’t.

This isn’t some Nate Silver quantum computing. Use this fuzzy math with caution. It’s one person’s insight based on hundreds of variables. And I already told you what I thought about people who make generalizations.