by Yoon Cannon | Build Your Dream Team, Business Growth Tips Blog, General, Management-Leadership, Marketing and Sales Blog Posts, Outsourcing and Hiring Tips Blog
SECRETS TO ATTRACTING TOP SALES TALENT FOR SMB OWNERS
There is a growing crisis in sales talent. According to Forbes, companies are “struggling to keep the sales reps they have, and having an even harder time finding and developing sales reps to replace them.”
Recruiting and retaining top sales talent has always been challenging. But, if you are trying to grow a small or mid-size company, it’s an added struggle to compete with the bigger salaries Enterprise companies can offer.
To help you attract top sales talent and navigate this era of the Great Resignation, I’ve rounded up six SMB owners to share their advice how they overcame specific constraints to recruiting sales talent.
SALES HIRING CHALLENGE #1. Hiring Salespeople Who Can Produce Quickly
How ClickGuard Overcame This Challenge:

Hiring is tough and in 2022 hiring the right sale people who can produce and ad value quickly is even tougher.
“I’m a strong advocate of hiring and building teams
based on the right culture for your organization” ~ Ralph PerrierClick To Tweet
Sales is a competitive sport, and like any good general manager, you should recruit and evaluate candidates based on their track record.

Hire candidates that are already active within your industry with a strong social network of relevant contact which you can benefit from.
Ralph Perrier, CEO of ClickGuard
Protect Your Google Ads from Bot Clicks,
Click Farms and Competitors and Prevent Waste.
SALES HIRING CHALLENGE #2. Limited Budget and Limited Local Talent Pool
How Function Fox Overcame That Challenge:

When we hired our first sales team – we are looking for people physically in our geography, so it was a limited market and we didn’t have big budgets.

We hired a former chef who had never really worked in an office before. He became one of our top performers and stayed with us close to 10 years and even got a FunctionFox Tattoo!
We always try to “Stay Creative” with any challenge that comes our way.
Corina Ludwig, President/ Partner – FunctionFox.com
Timesheet and Project Management Software
SALES HIRING CHALLENGE #3. Finding Salespeople Who Were Willing to Hold Themselves Accountable
How Green Rope Overcame That Challenge:

The biggest challenge we faced was finding salespeople who were willing to hold themselves accountable (fortunately, we have a great team now).
We have focused our energy primarily on inbound marketing, which is conducive to having a team of farmers.

Farmers are generally better with accountability and providing the data needed for closing the loop on the customer journey. Hunters tend to be more outgoing, extroverted, and harder to keep track of. We have found this role has been the hardest to fill and keep and are still in search of a good one.
Lars Helgeson Founder / CEO, GreenRope
All-In-One CRM with Marketing Automation
SALES HIRING CHALLENGE #4. Managing Budget & Expectations of the Sales Team.
How WeStrive Overcame This Challenge:

As a first-time tech founder, the biggest challenge has been managing the budget and expectations of the sales team.
To overcome this, I’ve taken the time to meet with people who have been in my shoes before.

Cory McKane, CEO at Westrive.com
The All-In-One App for Personal Trainers
SALES HIRING CHALLENGE #5. Making the Pivot to Enterprise Sales Teams
How Read Cube Overcame That Challenge:

ReadCube is part of Digital Science, which is part of the broader Holtzbrinck Publishing conglomerate. People who work in the Science Technical and Medical (STM) sectors know that Digital Science is a hot commodity.
So, I leveraged three core ways to be able to attract top sales talent.
- I engaged my network looking for potential sales candidates who already had a rolodex.
- The sellers I recruited worked for me in a past professional life, so we had/have mutual respect for each other.
- I also worked with a headhunter.

From those tactics I was able to source 15-20 top qualified candidates to interview.
Miles McNamee
Senior Vice President – Enterprise Sales, ReadCube
SALES HIRING CHALLENGE #6. Not Getting Enough Candidates
How DSP Helps Companies Overcome This Challenge:

In our 15 years in business we have been through many challenging times such as a recession and Covid 19. 2022 has been just as challenging, the challenge this time is finding quality talent.
Only 4-5 years ago if we contacted 20 potential candidates we would get 10 quality resumes. Today, if we contact 50 we are lucky if we get 1 strong candidate. What we have done to combat this situation is think out of the box and consult with our clients to do the same.

Although the clientele might be different the core processes and sales cycles are the same.”
Jim McKenna, President at Definitive Search Partners
We Partner with You to Bring You the Highest Quality Candidates!
SALES HIRING CHALLENGE # 7. Candidates Who Change Their Minds
LinkedIn recently published the top challenges facing recruiters. A staggering 75% of recruiters report they’ve dealt with candidates who went through the entire interview process, only to then change their minds last minute. (Ugh!) Unfortunately, this is growing problem that’s been happening at an increasing rate in the post pandemic world we are living in today.

How Yoon Cannon Helps SMB Owners Overcome This Challenge:
While it is unrealistic to completely eliminate this problem you can expect to greatly reduce candidates changing their minds by focusing on the big rocks I call the 3 R’s:
- Remote Options: The latest studies are finding that 56% of candidates turn down jobs because of lack of flexibility to work remote. They want flexibility more than they want pay and security. Where we have been able to help SMB owners is by designing systems to help you effectively manage a remote or partially remote team while boosting their sales performance.
- Retention through Relationships: Working remote certainly gives your sales team greater work-life balance, but it can also lead to your sales team feeling too isolated and disconnected. Pandemic or not, never forget human nature has proven throughout history that people will often stay with a company longer, not necessarily, because they love the actual work they do, but because they love the people they get to work with.
- Introduce candidates throughout their interview process to multiple managers and peers in your organization.
- Show the vibe of your people and the camaraderie they enjoy through your company videos.
- Create and showcase several videos of you, the founder as well as your leadership team. Don’t make it “corporate”. Be your genuine selves. Candidates will want to work for you if you give them ways to feel like they got to know, like and trust you.
- Recruiting Funnel: There is no one reason why a candidate changes their mind last minute. There are multiple reasons.
- Skills fit
- Personality fit
- Financial fit
- Timing fit
- Lifestyle fit
- Future fit and
- People fit / Culture fit
So, by the time you are reviewing your top candidates you can be confident each of those candidates have determined for themselves the role they are applying for is truly the right fit for them.

Yoon Cannon, Business Growth Coach,
Founder, ParamountBusinessCoach.com
Helping entrepreneurs scale your business growth!
SALES HIRING CHALLENGE #8. Generating Enough Sales as a Startup to Hire Sales Talent Without Any VC Funding
How Peeva Overcame This Challenge:

FIrst off, to make sense of this here is an analogy. Startups are like rock bands. Whereas, rock bands will send out demo tapes to whatever label will throw money at them. StartUps send out pitch decks to whatever VC will invest in them.
Either way, most of them never make it out of the garage. To get a record deal in your favor, getting out of the garage and touring is the best way to do this.
Investors want to see traction and there is no better way to show this than to have paying customers. It doesn’t matter who you know. People with money have it for a reason, they don’t spend it foolishly. Ironically, the far majority of VC funded companies also fail.
My best advice to any Entrepreneur is to get as many paying customers as possible and as quickly as possible. This also comes at great cost if you are irresponsible.
Peeva’s approach is a top to bottom approach.
Rather than hire a ground swell of boots on the ground (outside sales professionals) to make cold calls and hand off marketing literature and then pay them to chase and bother busy prospects, it was much more productive for us to establish a beta relationship with a large corporate chain of vet hospitals.
From the C-level down, we were then able to scale at a much quicker rate with veterinary professionals and hospitals without ever meeting them let alone speaking with them. Our veterinary professionals essentially do sales for us, by selling Peeva to pet owners.
I did all of this myself, before requiring any sales professionals. It was not until after I established these types of accounts before brining on a veterinary relations director that overseas 3 other sales professionals that follow the traditional meet face to face sales model. No VC needed, and the only VC’s I ever speak with at this point are those that reach out to us.

I hope this helps many entrepreneurs that will go broke or focus on an exit strategy before getting started.
Michael Hamilton, CEO / Founder of Peeva
Universal pet identification and central database
SALES HIRING CHALLENGE #9. Sales People Who Are Transactional
How Qnum Analytics Overcame This Challenge:

The biggest challenge in hiring my first sales team was the transition from their past selling “norms” into trusted advisors that would solve the customers problems as opposed to selling our products and solutions.
I hired sales talent who had the desire and hunger and weren’t too worried about their sales track record as that was in the past and CVs are exactly that past achievement. I was more interested in how I can transform the potential that existed to meet what our customers needed. So, I trained them to be consultative and not transactional.

Bheki Nkomo, Founder, Tech Entrepreneur Qnum Analytics
Digitize end to end inventory data capture
SALES HIRING CHALLENGE #10. Attracting Highly Motivated Sales Talent
How Fin vs Fin Overcame This Challenge:

The key is well-structured, performance-driven incentives. Why not offer unlimited upside to grow your business?
Of course OTE must be achievable so that your team can accurately forecast income and plan their lives. But incentivizing sales talent to treat your business like it’s their own has been the single most important thing. How can you make them feel more like an owner, rather than a rep?

Alex Goldberg, Founder Fin vs Fin
Discover the best wellness products
SALES HIRING CHALLENGE #11. Making Our First Sales Hire
How Conmitto Overcame This Challenge:

It’s easy at first to try to go too big, too fast especially while building a solution or consulting business. While growing an early sales team, it usually works well to start with one great sales professional to help you begin bringing your product or service to market.
Early on, it’s about learning quickly and allowing the sales, marketing and product development cycles to evolve together. It’s more difficult to do this with a large team in place, and I’ve seen firsthand how painful it can be to change or adapt once you’ve made a few great but potentially mistimed hires.
That will help you define and grow your offerings to fit the needs they’ve seen solving this problem first hand.
Based on the approach that works, it may make sense to hire more sales professionals with a similar background, or it may make sense to partner with a larger firm that is in the industry that can be trained to cross-sell or up-sell for you.

There’s no one-size fits all method, and you may find that direct sales hires, outside SDRs that focus on meeting generation, or a partner channel oriented approach work for you, or a healthy mix of the three may be the best approach. It’ll all depend on your industry and the state of your business, so the first step is to start trying and learning!
Akash Agarwal, CEO, Conmitto
Configurable cloud software for supply chain management
SALES HIRING CHALLENGE #12. Creating a Large Team of Sales Advocates as a Startup Company
How Aqai Overcame This Challenge:

Having been an entrepreneur for over 20 years, growing and scaling multiple teams and companies, sales is the lifeblood for growth. The challenges in hiring great salespeople and teams have evolved over the years. In my latest start-up at AQai we have focused on two key aspects to grow our company through a specific sales and go to market strategy.
Firstly, having a compelling mission, one that deeply resonates and connects with our audience of coaches and HR leaders. This driver to inspire & empower every human with the skills to adapt and thrive. Ensuring no-one is left behind in the fastest period of change in history, has been the corner stone to attracting truly great talent.
The second and important strategy has been to empower a global network of distributed agents to act as our sales advocates. With this strategy we have managed to rapidly train, certify, and enable over 200 coaches and consultants to win more business, and do more interesting work. With their sales and success, driving exponential growth on our adaptability assessment and training platform. This strategy has removed the traditional thinking for hiring, and the barriers of initial funding the growth of a direct sales team.
Using this strategic approach has enabled us to land significant projects with companies like Microsoft, IBM, The Federal Reserve Bank and Havi, among many other pioneering, people focussed organizations.
To find out more about our work, the community we are building focussed on the mental health and wellbeing in the future of work, please check out www.aqai.io

Ross Thornley, CEO & Co-Founder AQai
Change, retain and prepare your people for change
SALES HIRING CHALLENGE #13. Making Sure We’re Hiring the Right Kind of People to Fill the Role.
How Sched Overcame This Challenge:

The biggest challenge we’ve faced in hiring sales talent is making sure we’re hiring the right kind of people to fill the role. Sched helps individuals and teams create great events with our event scheduling software.
We invest significant resources in training our sales team to be able to offer solutions for our customers’ challenges when trying to plan great events.
We want to make sure our salespeople can uncover problems, explain our solutions and build trust along the way.
Instead of just hiring a Sales rep, we are trying to hire people who over time can expand their roles. Our company is remote, distributed and filled with self-motivated, accountable people. We look for bright, hard working, results-oriented individuals with high levels of integrity because they are the most likely to succeed within our team. Finding these people makes our typical hiring process look more like an audition than the typical “application and interview” process. Hiring good people is tough. Hiring good sales people is even tougher. Our hiring process helps reduce some of that risk and increase the probability of a successful sales hire.

Marvin McTaw, CEO of Sched.com
Event Scheduling Software & Event Mobile Apps
So, there you have it. Thirteen founders sharing their personal advice on how they overcame specific Sales Talent Hiring challenges.
▶ QUESTION: What specific hiring challenge would you like to see covered in this article? Please share your comments below.
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by Yoon Cannon | Build Your Dream Team, Management-Leadership
How to Build a Dream Team as an Entrepreneur (for Startups)
The purpose of this guide is to help you build your startup from a team of one to a team of many. You’ll know how to identify your startup needs, find the right people to fill those needs, and how you can bring those people together to create a high-performing team.
If you want to get your ideas off the napkin and on the ground running, it can be helpful to prioritize the growth of your team. These are people that you can mold into your workflow, and bridge the gap between your expertise and business knowledge. Not only will you have to expand it, but also make sure these individuals have a strong foundation to launch from.
Have a Clear Vision for Your Startup
If you’re reading this you probably have an ideal plan for your business, but the development of a business idea still has to be completed. Either way, solidifying the vision is a great first step toward a clearer direction.
Once you’ve outlined your idea or “vision”, set SMART goals for building your future team. As a refresher, these are goals that are specific, measurable, achievable, relevant, and timebound. They can always be adjusted throughout the different stages of your startup so don’t limit yourself, or feel limited to sticking to your original plan.
During the stage of crafting your business’s vision, find individuals to network with and learn from. They may have gone through a similar process before, or have a well-rounded knowledge of establishing a startup. If conversations go well, and you build trustworthy work relationships with others, you can always further the mentorship process and ask them to be an advisor for your startup team.
These don’t have to be full-time employees, but more of a mentor or phone call away if you needed a helping hand. Without one, you could be missing out on necessary industry and experience-based knowledge so take additional time to prioritize those networking events, and connect with as many people on LinkedIn as you can!
Once your advisor or board of advisors is established, make sure to take the time to review expectations and schedules with them. Take their areas of expertise and experience into consideration when developing a strategic plan for your business. ask questions such as: How involved will they be in the process? Will there be weekly or monthly meetings?
Evaluate Your Startup Needs
As an entrepreneur, you may pride yourself on being self-sufficient and independent, but you doing everything by yourself can actually lead to burnout. Skills that you may lack, another person could really excel at. Instead of thinking that you can do everything the best way, delegate the tasks to other people and work along with their strengths to help build your business.
Write down what skills you can improve upon, and what the main needs of your business are, and find the gaps in between each to create roles for your future team. Remember, self-awareness and honesty are key to benefit from this exercise.
Hiring people who are different from you helps to create a well-rounded team with a diverse skill set. Diversity leads to more creative solutions to problems. Hiring people who are not only equipped with different skills and backgrounds but also different personalities and interests can lead to more success. While keeping diversity in mind, there are a few key abilities and traits that you should also look for when bringing on team members.
First and foremost, startups can be completely unpredictable. Most of the time, they may be strapped for resources, tools, and possibly money. You will want people who can bounce back from mishaps that are bound to happen when you’re working in a company that’s in its early
stages. People who are adaptable, innovative, and capable of multitasking will thrive in this ever-changing and evolving work environment.
Use Your Connections to Your Advantage
This may seem obvious, but making connections is essential when you’re recruiting new business team members. Take advantage of networking events, industry-focused workshops, and other opportunities that may broaden your social reach.
As mentioned earlier, it’s important to first find someone (or maybe even multiple people) you trust to serve as an advisor on your team. Depending on what you’ve identified as your business needs, you’ll need people to fill those roles. Typically, the starting lineup of any company will include these positions:
- Chief executive officer
- Chief marketing officer
- Product manager
- Chief financial officer
- Chief technology officer
- Business development manager
- Sales manager
- Customer service expert
However, don’t feel tied down to building your dream team around these positions. You can adjust or delegate multiple roles to team members.
If you feel like the number of connections is looking limited, don’t hesitate to use hiring platforms to build your team too. Indeed, Linkedin and Glassdoor are reliable for finding and recruiting top talent. If you’re not confident using this method by yourself, consider involving your advisor in the hiring process. They can assist you in interviewing and choosing candidates, and it never hurts to have a second opinion on something that’s going to affect your business.
Another thing to have handy in the hiring process is an employee checklist for candidates you’ve decided to move forward with. You’ll want to make sure your employees are set up for success early on in your business beginnings. On the note of successful beginnings, make sure your team is properly compensated whether it’s monetary or otherwise from the start of employment.
Take your advisors, for example, they’re not just doing you a favor by mentoring you through your startup journey. There are a few ways to go about compensating advisors, one of the most common is to utilize the FAST Agreement from the Founder Institute. This is a flexible approach to providing compensation as it depends on the company’s maturity and the level of advisor engagement.
As for your other team members, you may be wondering how you can not only compensate top talent but also entice them to work for you. For startups strapped for financial resources, it might seem like working for a startup is undesirable. Job seekers might opt for work at a larger company with higher pay and better benefits. But, how long does it take until those benefits are outweighed by a lack of satisfaction?
It all depends on an employee’s value, and how they are able to connect with your start-up’s overall mission. Even though a larger company is most likely more established, it does not mean they are prioritizing employee growth and opportunity. It’s all about how you advertise your business to those who you want to hire. Relate to an audience and show them that, even though you’re smaller and in a more development phase, it could give them a lot of experience!
Working at a startup and on a smaller team fosters a sense of belonging and purpose as well. There is a clear goal for the team to work towards, and reaching that goal is the most satisfying feeling. Furthermore, a startup with a clear vision and personable leadership is more attractive than a big corporation with less than ideal morals and goals. As stated earlier, a startup may lack resources and constantly change. That isn’t necessarily a bad thing though, it gives employees a challenge that they can benefit from professionally.
Making and utilizing connections is an effective way to form a team but it’s also crucial for finding support outside of your internal team. You’ll need people to advocate for your startup to help you achieve your goals. Accelerator programs are a great resource for breaking through a heavily saturated market.
Rafael Ilishayev and Yakir Gola, co-founders of the delivery company Gopuff, understood the importance of having an advocate in the early stages of a startup through their small business accelerator program. These are great for business-minded people who are starting their own companies because it gets them in front of the right people to find funding or other resources that can set them up for success.
If you’re looking to expand, take advantage of the resources and opportunities that these company-created programs give you especially as you’re growing your team. And who knows, maybe one day you can give back to the entrepreneurial community with your own accelerator program or fund!
Instill Strong Values In Your Team
When you have finally assembled your team, consider having them take a personality assessment. This test can give you an idea of how individuals will work with you and the rest of your team. Remember, it’s less about who is on the team and more about how the team works together. Once you’ve done this, you know how your team can most efficiently work together.
But, that’s not the end of things. What foundation are efficient and high-performing teams built on? A few things; trust, consistent communication, respect, and honesty. If your team consists of people with all these traits, they’re more likely to be there to support you and each other. From day one, you need to set up the expectations of these values for your team.
Re-evaluate Your Team as Needed
Now that you have your team and know how best to work with each other, it’s important to keep track of your progress as a business. If you find your team is missing something, like a specific skill set or perspective, consider bringing someone on to help. You can either hire someone to fill a role on your internal team or you can outsource an individual or an entire team.
Let’s say you’re lacking the marketing tools to propel your business and you find your team unsure of how to tackle this issue. Ask yourself, “Do I hire a team to do in-house marketing, or should I outsource?” While there is no right or wrong answer to this question, and it depends on what works best for your business, this outsourcing vs hiring guide may help you find perspective on what to do if you find yourself in a situation like this.
At the end of the day, your team is what makes or breaks the success of your startup. Hence the saying you’ve probably heard countless times, “Teamwork makes the dream work!” By utilizing the tips mentioned above, you’ll build the startup team of your dreams in no time.