July 24


Sales Team Hiring Guide

By Georgia Davis

July 24, 2019

Sales Team Hiring Guide

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As a small business owner, you’ve always been your company’s head of sales—not to mention trouble shooter, receptionist, light-bulb changer and, oh yeah, founder and owner. But now the company's grown to the point that even you recognise you cant do everything. It’s exhilarating -and terrifying. A salesperson is someone you’ll rely on not just to expand your customer list and your sales, but to tell your company ‘s story every day.

For a head start on finding just the right person to fill those gigantic shoes, consider the tools and guidance in this helpful guide full of practical tips.

7 Things to Look for In a Quality Resume

The resume has been around for more than 500 years—and not even the digital age has lessened the vale of this straightforward tool for separating good candidates from bad. For small business– owns, it’s the ultimate hiring brief and best place to start your evaluation process.

Sure, there are resume qualities that apply to most jobs. For example, resumes that list experience only by year could be hiding gaps of several months in between jobs—possibly signalling someone who has trouble holding positions or who quits when things get tough. However, there are elements that apply more specifically to sales.

What can a resume tell you about a person who has what it takes to become your enthusiastic partner in growing your company? Whether you review the resume on paper or through an online resource such as LinkedIn, these seven qualities can help you determine who to call in for a formal interview.

Meeting and Exceeding Goals

Success in sales is largely about
numbers, and good salespeople will
proudly display them on their       resume. If they’ve operated on a
monthly quota, how frequently did
they exceed that number? If they’ve
had a hand in expanding market
share, how and by how much? Did
their sales increase over time?

Expanding Territories

Looking for signs of steady progress
toward goals such as larger territories, more prominent roles and new challenges. Have candidates consistently pushed new verticals?

What evidence do you see that they are always thinking about growth and expansion—for themselves and the business?


Unlike some professions where
recognition is more subjective, sales
awards are usually tied directly to
measurable performance. A candidate who has been recognized for excellence by her company or industry will likely repeat that track record for you.

Entrepreneurial flair

The sales person you hire will in
some ways have to invent his roles,
helping you develop processes and
build a sales structure for the team.
Someone who's spent most of his
time as a salesperson or manager at
a very large company accustomed to
formal procedures, may feel lost in a
start up environment. Evidence that
he’s thrived amid entrepreneurial
uncertainties could be a plus.


A huge part of sales rests on the ability to catch and hold the attentions of customers and prospects. Does the resume move crisply from point to point, covering the highlights in succinct, active prose? Or does it explain ancient experiences and minor accomplishments in exhaustive, jargon -heavy detail? 

Though not everyone speaks the way they write, a resume that bores you could be a warning that customers will feel the same way in sales meetings.

Attention to Detail

The person you hire will soon represent your company and your brand in front of the people who matter most: your potential customers. Typo’s and
grammar errors are a clear red flag.
Will candidates who cant be bothered to proof read their own resumes share a fanatic attention to detail that’s making your company successful? Is the resume logically prepared, easy to follow and visually

Excitement (yours)

Of course, you cant tell everything from a
resume. But because the purpose of these
documents is for the candidate to sell you on
the idea of a formal interview, ask yourself if
this is someone you cant wait to meet. If so,
you may be on your way to finding someone
who will help you take your sales, and your
company, to the next level.

And one thing you thought
mattered (But probably doesn't)

Many job descriptions demand industry experience.
Although small business or entrepreneurial experience
can be a big plus (see above), intimate knowledge of a
particular product or service can be overrated—and
demanding it will limit your proof of skilled prospects.
The human qualities that make a great salesperson—
energy, passion, ambition, honesty, creativity—travel
well from one company to another. It’s better to seek a
great salesperson and bring them up to speed on your

The Ultimate Interview Question Guide (And Answers You Want to Hear)

5 Questions to Ask on a Phone Screen

You’ve sifted through a stack of resumes and developed a manageable list of talented prospects. The phone screen is your first opportunity to hear a human voice, get a sense of personality and style, and narrow the field to a few choice candidates you’d like to interview in person. The responses to question can tell you a lot.

1. What is your current status - and why are you looking to make a change?

This compels candidates to explain why they are interested in leaving their current job, or why they left the last one. Look for positive, forward looking answers rather than gripes about the mean boss or unfair conditions at their current job.

2. Why do you want to self or a small business?

Selling for a young company and a multi-billion dollar enterprise are entirely different prospects, each with
distinct advantages and drawbacks. You want someone who particularly relishes the opportunities (and risks) of entrepreneurship—not someone simply looking for another sales job.

3. What do you love about sales?

This gets to the heart of their motivation and invites them to tell a story of their passion for selling. Look
for someone whose enthusiasm for the profession leaves you inspired. It’s a good sign that they’ll be
able to inspire potential customers with the story of your company and it’s products.

4. What do you know about our company

The answer can tell you whether the candidate is serious about the possibility of working for you. Unless
you’re calling out of the blue, he or she should come to the phone having done some basic research, starting with a thorough reading of your website.

5. Are you open to working mostly on commission?

Or, “How do you feel about frequent travel?” Or, “Would you be happy living in a small town?” Whatever idiosyncrasies the job (or your company) present, use this call to identify deal breakers before going through the trouble of an in-person interview.

5 Questions to Ask During in Person Interviews

Now we’re getting close. Here’s your chance to dig on what moves them, how they define success and respond to adversity and whether they’ll be a good fit for your company.

1. Describe your sales process

Sales is part art, for sure, but any good seller has tried and true processes for producing repeatable results. Candidates should discuss such points as how they generate leads, how they differentiate between leads and qualified leads (those with a need for your product and the capital and authority to say “yes”), what techniques they use to close a deal and how they follow up with customers after a sale.

2. Sell me this pencil ...

There’s nothing like a little sales role-playing to tell you how a candidate thinks on his or her feet, says Lou Caporaletti, Director of Lead Development for Keap®. “It can be a little awkward, but that’s okay. You get a good sense for somebody’s selling technique, how effective they are and how well they’ll communicate with prospects.”

3. How do you stay in touch with your customer base?

There’s no substitute for face-to-face visits and personal calls. But have they also found effective ways to use email and social media to update clients on industry trends and new offerings and to keep track of their changing needs?

4. What single sale are you most proud of?

Was the high point landing a customer every one said was impossible? Repairing a broken relationship? A sale that came only after months of effort? One that required working closely with a team? Depending on your prior ties and your company’s culture, this question may help you determine if he or she will be a good fit.

5. How do you respond when you lose a sale?

Don’t settle for clichés or platitudes. Ask your candidates for a specific example of how they responded to adversity. What did they learn that helped them get better? Were they polite to the prospect in the face of rejection? Are they likely to obsess over each failure, or do they find productive ways to vent, pick up the pieces and move on? Do they maintain that relationship for a future opportunity?

5 Questions to Ask References

Yes, references are handpicked by the candidate and unlikely to say anything negative. But that doesn’t mean they are a whitewash. Ask for names of customers as well as managers. Beyond confirming work details in the resume, these interviews can offer valuable insights, provided you ask the right questions.

1. What was this candidate’s strategy for building sales?

As a growing business, you need more than an energetic, personable rule-follower. Did he find new ways to expand his target market and reach out to potential customers — or simply conform to a corporate playbook? How did he build and expand existing customer relationships?

2. What makes him or her a great salesperson?

Terrific sales people come in many varieties. Is it her passion for the product? His love of solving people’s
problems? Persistence is a must, but if phrases such as “bulldog” and “never takes no for an answer” come
up first, consider how those qualities will jibe with your culture, your target customers and your brand.

3. How did he or she handle customer dissatisfaction?

Even the best salespeople sometimes face angry customers. Knowing how the candidate has handled these situations in the past offers a window on how she’ll represent your company in a tough spot. Ask for a specific case. Did she accept responsibility and go out of her way rectify the situation, even at cost to herself? The answer may reveal whether she’s interested in building long-term relationships or just focused on next month’s numbers.

4. How did the candidate work with others?

Sales is a competitive profession that attracts people who are out to show the world they’re the best. That’s great, but a focus on self over team may be best suited to a large company where the products and strategies are dictated from on high. As a small business, you need someone who will not only be driven to succeed but who will also help you craft a sales strategy and have a deep interest in communicating that vision to others in your company.

5. Would you hire/work with/buy from this person again?

This is a good way to end the conversation, compelling a personal reaction that they may not have been expecting. Since the candidate supplied the reference, you’re unlikely to hear, “No way!” Still, the difference between a hearty “I’d do anything to get him back” and a hesitant “Well ... sure” speaks volumes.

Sales Team Playbook: How to Attract and Retain Top-Notch Sales People

OK — so now you’ve identified the salesperson or small team capable of taking your company to the next level.
Congratulations! These are the people who will put your strategy into action, helping existing customers and prospects understand why they need your products in their lives.

Now, it’s time to concentrate on helping your sales team shine, making them great and keeping them happy. That includes structuring the right day strategy, giving them the proper tools and making sure your new hires leap out of the gate with a terrific first year.

How to Pay Your New Sales Team

In an imperfect world there may be no such thing as the perfect formula for paying your new sales team. But the one that comes closest will keep them motivated to work hard and grow with your business, while still offering a bit
of security during the inevitable times when the salesperson hits a dry spell or the market suffers.

Put it in writing

Among the attractions of working for a small business are flexibility, informality and a we’re-all-in-this-together sense of trust. So it may be tempting to outline your sales compensation policies in a quick conversation with
potential hires and assume all is understood. But that’s a recipe for misunderstandings that could destroy the relationship.

Instead, craft a formal written document that you review carefully with any salesperson you bring on board.

This should include:

  • Your company’s overall mission and goals (borrowed from your business game plan). Sales isn’t just moving units — it’s an extension of who and what you are as a company.
  • How he or she will be paid, whether the emphasis is on commission or salary.
  • How you’ll measure his or her performance.

Salary or commission?

A happy, motivated sales force means striking the proper balance between base salary and commission.

  • A pay model based on salary offers predictable, reliable income and may create a loyal, stable staff — but complacency is the enemy.
  • Commissions offer the upside of higher income for ambitious sellers — but could leave them fretting over rent if they hit a dry spell.

While there’s no preset formula, “a good rule of thumb for a smaller business is to be heavier on commissions and lower on the salary,” says Lou Caporaletti, Director of Lead Development for Keap®. “Small businesses often have less capital to spend on salaries.” Just as important, he adds, “Good salespeople really thrive in an environment where they can in essence create their own paycheck. I’d be wary of hiring any salesperson who wanted to be paid mainly in salary.”

You might consider a formula of, say, 30 percent of their compensation coming from salary (enough to offer a modicum of reliability) with the remaining 70 percent from commissions based on a percentage of sales. Say you settle on a commission level of 10 percent of sales. To keep them striving for growth, set a policy that sellers receive the full 10 percent only if they reach whatever sales quota you set for them, Caporaletti suggests. You might bump commissions on sales above the quota to 15 percent or 20 percent. “They’ll really work hard to beat quota,” he says. By the same token, work in a penalty for sellers who fail to reach quota. How do you set that quota? Glad you asked.

Measuring performance It’s not enough to unleash your new sales team with a pep talk and the admonition to “go out and sell!” Establishing the right sales quotas for your company involves as much art as science, especially when you’re hiring salespeople for the first time. Set the bar too low and your salespeople may take their foot off the pedal. Set the bar too high and you may engender resentment when a talented salesperson comes up short. The best way to determine workable quotas is to closely examine your own record over the past few years. “Chances are, you’ve got a pretty consistent level of sales,” Caporaletti says. Beyond sales, think about how many leads you’ve been contacting each week and how many new ones you generate.

Consider your sales cycle (i.e., how long it typically takes between initial contact and closing the sales.) By quantifying these points, you’ll be better able to set ambitious but realistic goals for your staff.

7 Tools and Tips to Help Your Sales Team Succeed

Just as your products are only as good as the parts or ingredients you put into them, your sales staff is only as effective as the resources you provide. Giving them clear guidance, instilling them with the passion of your
company, and offering tools, resources and best practices helps make their challenging job more certain of success. Consider adding these potent weapons to your team’s arsenal.

1. Customer relationship management

Any good salesperson knows that collecting and organizing customer and prospect data is the best way to prioritize leads, schedule follow-ups and build relationships. But it’s also time-consuming for sales staffers who need to be out in the field in order to be effective. Investing in top line customer relationship management (CRM) software such
as Keap® CRM for Small Business can automatically collect data about leads’ behaviour, score leads based on those most ready to buy, track appointments and needed follow-ups, help your sales staff better understand and address customer needs.

2. Marketing automation

The only lead guaranteed not
to bear fruit is the one you or
your sales team fails to follow
up on. But creating personalized
messages by hand can eat up a
salesperson’s entire day. A good
marketing automation system
can help you maximize customer
engagement by creating
personalized communications
based on email sends, opens,
clicks, and the like. Systems
such as Keap’s Campaign
Builder enable you to customize
approaches to meet highly
specific marketing goals.

3. Streamlined processes 

Any professional job has its share
of administrative processes, and
sales is no exception. But your
sales team is happiest (and most
effective) when they’re out doing
what they love to do: engaging
customers and prospects.
Automating your processes can
help them do just that. Consider
a software system such that
enables you to seamlessly create,
manage and email customized
quotes and proposals to
prospects, which they can click
on to accept — thus saving your
sales team valuable time.

4. Demos and materials

Demonstration is a key to sales
— the difference between telling
someone why your product is
great and showing them why
they absolutely must have
it. Depending on the nature
of your products or services,
make sure your sales team has
the best demo models, online
presentations and slide shows
to highlight the advantages of
buying from your company. And,
since your business may change
frequently, be sure to keep these
materials up to date. Sending
sales reps out with outdated
models and specs makes them
look unprofessional.

5. Content

In the internet age, studies show
that the vast majority of customers
and clients research on their
own before making the decision
to buy. Content in the form of
articles, checklists or videos that
you post on your site or make
available through social media or
other channels can help establish
awareness of your brand. As
distinct from advertising, content
is aimed not at direct selling but at
building trust and reputation. The
more comfort people have with
your brand, the easier it will be for
your sales team to close deals.

6. Updates and team-building

Though sales is a profession for
individual achievers, you can
help your sellers get better by
fostering a sense of teamwork
and encouraging the sharing
of best practices. Make sure that your sales people interact
regularly with others on your
staff to help them soak up the
culture. And be sure to invest in
training update programs that
introduce your team to the latest
technology, or further develop
their professional skills. This will
pay off in the long run, not just by
making them better salespeople
— but by building loyalty in your
company by communicating that
you are interested in seeing them
grow and succeed.

7. Celebrating success

What drives a first-rate sales team? Money, of course, but
also recognition. You can reward productive sellers and also instill healthy competition on your team by calling out sales leaders with monthly or quarterly awards. Hold
an annual dinner or barbecue to formalize the awards. And spread them around — note improvement as well as top performers. You’ll encourage your best members
to strive further, and your weaker ones to improve.

A First Year Roadmap for your Sales Rep

Having a salesperson is an investment in your own future. Make the most of it by giving that person a clear path to success starting immediately and continuing through that crucial honeymoon year.

Upfront training

Let’s be clear what we mean by training. If you need to train them how to sell, you may have hired the wrong person. Caporaletti notes, ‘A small business needs an A-player who can take over your sales and teach others
you hire. But do you take the time to educate them on the nuances of your product. A salesperson who hems and 
haws about key aspects of your product or services will instil similar lack of faith in your customers about your
quality and attention to detail. Before you set them loose, ask them tough, specific questions and gauge their
answers to make sure they’re ready for prime time.

Solid leads

Nothing frustrate a sales person more than expending creative energy attempting to sell a prospect who has no
intention of buying, no matter what. Shortly after hiring your first salesperson, you may even want to hire a
“lead qualifier,” Caporaletti suggests. This can be a younger, more junior employee who spends his or her days
vetting leads to make sure your sales teams spends its valuable time on the most promising prospects.

Set incremental goals

By the time you bring a sales rep on, you should already have mapped out a quota for the year ahead that you expect him or her to attain. But don’t expect it to happen all at once. You might divide the yearly target
into quarters. Create a smaller (but still measurable) goal for the first quarter, leaving room for training and getting comfortable with the processes. You might tie performance to pay, Caporaletti suggests, by promising them
they’ll be bumped up to a higher commission rate if they achieve first-year targets.

The room to succeed

This tip doesn’t require much from you except a commitment to strategically know when to back off — and that may be the toughest thing of all. After all,  nobody knows the company, products, or customers better than you do, and you will feel tempted to manage your salespeople’s every move and monitor their relationships. But there’s a difference between staying aware and micromanaging. Give them tools, guidance and goals, and then follow up to assess their results. But don’t hover.

Quarterly reviews

Reviews are a great idea for any sales rep — but for those who are new, don’t wait until the end of the year. Meet each quarter. You’ll be able to spot small problems and course-correct before they become big problems, Caporaletti
says. Note the successes, making clear what they’ve added to the company. And note areas where you see room for improvement — measured wherever possible against the goals you established when they arrived. The experience is still fresh enough that you can encourage change and growth in areas where they need improvement— and they
may have valuable insights to help the company get better.

The road forward

With a year under their belt, your sales rep is ready to surge into a new year as a seasoned veteran. He or she knows your processes and products inside and out and owns a contact list of valuable customers and prospects. It’s easy
to get busy and overlook goals for the new year until you’re well into the first quarter. Don’t. Now’s the time to set clear, ambitious goals for the year ahead.

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Georgia Davis

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