Founders: Ready To Hire For Sales? Learn Sales Hiring Tips To Minimize Your Risk On The Wrong Choice

Founders: Ready To Hire For Sales? Learn Sales Hiring Tips To Minimize Your Risk On The Wrong Choice

Have you heard all of the horror stories from other founders about hiring the wrong sales rep? The potential sales churn is real for a startup but knowing what qualities to look forward what to ask in an interview can help you avoid spinning wheels on the wrong hire. By the way, the expense with churning an Account Executive can be as much as 18 months of their salary. In tech startups that could be as much as $150k+ which can be detrimental to an early stage. Read these tips on how to find the best match for your org:

Indicators That Your Startup Is Ready For A Sales Rep

  • Do not hire anyone for sales until you have product-market fit and have sold at least 10 deals yourself as a founder. You must prove the sales process yourself. As the founder, you’re the only one that can bring the original passion to your product/service that will initially sell it. Once you validate product-market fit then you can teach your value prop, sales process, etc to a new sales hire to execute.
  • Is your customer lifetime value (CLTV) over $5k? If it is, then you’re more than likely ready for a sales hire.
  • If your CLTV is over $5k then you more than likely have a complex sales process that a rep can provide value in navigating. Great sales reps live and breathe problem-solving for their clients and will add the most value to your organization in this way.

Qualities To Look For In Your First Sales Hire

Startups need to scale and grow revenue so it makes sense to hire a sales team at some point. Here are some key qualities you need to really focus on feeling during the interview process to ensure they are a great fit for your stage in growth. There are great reps but not everyone is ready for the constant change and uncertainty that a startup environment can have.

Leadership Qualities: Coachable and desire for constant learning, inspirational, shows passion to make a big impact on the world vs. immediate large paycheck (outward focus vs. inward focus). Accountable for results. Can voice their career vision so you can evaluate their fit into the growth plan of your company.

Communication Qualities: Detailed communicator. Extroverts however introspective as they’ll need to be very flexible with customer personality styles. Your ideal customer may change while you continue to grow and pivot as a company. Empathetic, active listeners perform well.

Sales Style: To really understand a rep’s style, ask for examples of how they exceeded sales goals and delighted customers. Ask them about times when they lost a deal and how they handled it. This will tell you about their resilience and ability to handle the emotional sales rollercoaster. What does the sales rep do when they are handed leads? You want to hire someone that understands the importance of outbound prospecting vs. waiting for leads.

Consultative selling skills are required for startups. Being able to enroll your customers and solve their problems with your company’s solution will be critical. Ask your candidate to give you an example of when they were able to break into a new account, build a relationship that perhaps was looking at the competitor and convert them to a sale.

Culture Is King: This is so important as they will be holding the flag for your company, selling not just your widget but the story behind the widget. If they don’t feel comfortable or supported by your team and they are a high performer, they will leave prematurely on you so set them up for success by hiring for a good culture fit.

Check Their Network: Check with former colleagues and clients before you hire them. You want to hire someone that is delighting their customers, collaborating with colleagues, and making a positive impact in their work environment. Checking a person’s network can be done easily through LinkedIn if you aren’t already connected with them. See where they worked previously and make some cold outreach prior to checking the reference contacts the candidate gives you. Provides some additional context for your hiring decision.

I hope you find these tips helpful when looking to hire one of the first reps. It is a big step and if you’re reading this article, you must take it seriously. My mission as the founder of Relativity Sells is to help tech founders accelerate their revenue by translating their secret sauce to their first sales team and maximize rep performance through enablement. For more weekly sales tips or information please visit Relativity Sells or follow Amy Looper, Founder.

Relativity Sell’s Founder, Amy Looper Featured In Sales Hacker

Relativity Sell’s Founder, Amy Looper Featured In Sales Hacker

Are talk tracks just a fancy new tech take on sales scripts? Not according to these sales and sales enablement experts. Software tools are constantly improving their platforms with new features, new product lines and new uses cases. Talk tracks are a helpful tool for sales reps, both new and experienced, to practice new pitches, share new info and have confident conversations with their prospects.

Hold up: What is a talk track?

A sales talk track is an outline for sales reps to follow during meetings with prospective customers. While strict call scripts constrain an SDRs ability to guide meaningful conversations, too little structure results in reps winging it, resulting in missed opportunities.

“The most important sales conversation your rep has is the first discovery call. It should be used to truly understand your prospects needs, timeline, and how you can help solve their problems. By having a great discovery call, you are set up for a successful follow up meeting. Talk tracks play a huge role in your new reps’ success by providing them an outline they can rely on, and more senior reps can feel confident when they have a new product to sell or a new industry to break into.

Sales leaders know that selling is all about having conversations. Talk tracks give these conversations structure so your reps can focus on creating value, controlling the process and winning deals.

Sales enablement leaders like Amy Looper, Founder of Relativity Sells, recommend creating talk tracks collaboratively. Make sure “everyone agrees on the messaging, stresses value and ensures an understanding of the ideal customer profile,” she recommends. “The format and questioning used helps to qualify and disqualify leads.”

Don’t make the call about who you are, your company, and your product features. Talk tracks resonate when you talk about the prospect, not yourself.

Leslie Venetz, New Business Development Director at Procurement Leaders says starting out on the right foot is critical. “Too often I see reps starting their sales conversation with a run down of how long they’ve been with the company, where the company has offices, or a list of product features. Why would your prospect care?” She compares this to pulling out a resume on a first date. “Without learning anything about your partner, you started with a list of everything about you that you believe a stranger should care about. It would be off-putting.”

Do try to understand your buyers and actively listen.

“REALLY listen, and then build your talk track around the buyer,” recommends David Weiss, Regional VP of Sales at Seismic, “It should sound different every time, but with some core themes that are expertly woven in based on what you heard.”

Haley Szelkowski, SDR Manager at Thomson Reuters, agrees saying that, “just like in sports you need to be on the balls of your feet actively listening and adapt your track to what the client has said and build from there. If you go in with a script and are not ready to deviate from it… it’s hard to win any game that way.”

Don’t wing it. You won’t get the answers you need or present the value to your prospect.

It’s all about practice, practice, practice. Jack Wilson, Sales Coach/Trainer and Mentor at The Sales Rebellion, advises practicing, “until you internalize them to the point that they come across as natural and conversational as opposed to overly rehearsed and prepared. Don’t memorize the words, instead understand at depth what you’re really talking about.”

Do come prepared with a clear objective. Matt Scheitle, Revenue Enablement Manager at recommends building an objective or call to action into your talk tracks.

“Develop your objective or call to action, work with your product marketing team, and then A/B test your talk tracks at different levels. Most importantly make sure your talk tracks follow your customer journey and sales methodology.”

Enabling your sales reps with talk tracks

Talk tracks help SDRs succeed through thorough planning and enablement. But that can only happen if you create a centralized process for building, testing and training your reps on new talk tracks (with the right messaging). This ensures that reps are consistent and confident in presenting value to prospects.

How to build talk tracks

The first step is to brainstorm the framework for talk tracks with your reps, according to the Director of Sales at ClearCut Analytics, Jake Bernstein. “Talk tracks are often derived from particular challenges or objections reps receive in their outreach,” he explains.

Next, let your sales teams personalize their talk track. Joe Latchaw, Outbound Specialist at NTT Data, adds that, “just presenting your team with a script comes off as demanding. If they are included in the process, it will truly be a team effort.” Successful sales teams need the freedom to make talk tracks their own. “Most reps don’t want to read off a script, and customers don’t want a robot selling to them,” says Rich Adams, Sales Enablement Manager at Zoom.

Finally, remember that talk track enablement is not just for the sales teams. Be sure to include other GTM teams when testing out a new talk track. Jen Ferguson, Director of Sales at Inside Out, explains that, “with weekly reviews this allows us to see what is working and what isn’t. We adapt based on the voice of our customer, always shifting our approach for better results.”

How to train reps on talk tracks

How do you funnel all of this information into an effective training program? Distill it. The goal of training is not for reps to remember everything. Practicing realistic scenarios through role playing new talk tracks is a great way for sellers to learn the material.

This approach focuses on building confidence with new material, rather than memorizing line by line. Alicia Avrach, Sr. Director of Sales Productivity at Workato, shares how her organization focuses, “not so much on AEs using the story as-is, but more about them learning the key points. When the differentiators and pains become muscle memory, they can really focus on the prospect conversation.”

Not surprisingly, the best advice is to practice. Matt Scheitle says to, “give them cues to engage with based on different market verticals and personas. We then evaluate the performance of reps and review calls regularly in Chorus to make sure the talk track is landing with customers.”

As a sales leader, you should understand the new talk track just as well as your reps. Kelli Coughlan, Enterprise Sales Team Lead at ZeroFox, says it’s important to,”critique your own phone calls as well as the team.” Everyone speaking to customers needs to lean in because, “we’re naturally resistant to change,” reminds Derek Jankowski, Creator at Next Level Sales Leadership Project. “So understanding the purpose and teaching them the ‘why’ behind a message, helps them buy into the change.”

New talk tracks are needed for many reasons and reps will want to understand the rationale of introducing something new. Brain Wool, VP of Growth at StorySlab, says it could be, “something that’s occurring internally, like messaging not resonating, or a shift in the marketplace, like COVID-19.”

Confident reps who understand the messaging will show their prospects how excited they are about these new changes. T. Melissa Madian, Founder and Author at TMM Enablement Services, likens a talk track to a performance saying, “just like a movie script, a talk track is useless without emotion, passion and practice! Give your sellers the opportunity to learn their script, then let them make it their own so the buyer can feel their passion.”

How to build continual improvement into the process

Sales reps should continue to practice their talk tracks even after they complete their sales certification. Jake Bernstein says that his team will “share highlights after the talk track is put into action in group settings, or via Slack. We work to zero in on specific words and phrases that might work.” What does a successful talk track look like? “I look for positive responses or creative tension. You know your talk track is working if you gain agreement, or if you get someone asking questions to learn more. If you are getting shut down, or lots of redirects, you’re off base and not active listening,” says David Weiss. To see how SDRs are performing at a team level, Brain Wool says, “measure, measure measure. If you’re introducing a new talk track, there is a reason. Are you trying to generate more opportunities? If so, what’s your current conversation rate to meetings booked? After introducing and training the new talk track, did your metric increase or decrease?” Jack Wilson takes a straightforward approach when asked how he measures success. “Easy peasy, increase in both conversions AND no’s. If your tracks are good you get the truth which is that they’re either interested or not.”

Giving your sellers the content and tools they need

As Brian and Jack emphasized, it’s important to measure the success of your reps when using a new talk track. Sales tools can surface the fine details of a call and give much needed context for one-one-one coaching.

Best tools for enabling new talk tracks

“Gong is a great tool to track these types of things. But more than anything I love to be with my reps in the trenches. Nothing replaces real coaching and ability to pivot in the moment,” says David Weiss.

Matt Scheitle and his team use their own platform,, to effectively measure their success. He also finds that, “Outreach is great for emails, where their in-app reporting allows us to track and correlate success with the opportunities it’s tied to.”

In some cases, you can use a sales engagement platform, which Leslie Venetz says “helps build consistency into the talk tracks that are used for cold outreach.” Without a more active approach, it’s more limited but can get you on the right track.

So what about the more proactive options?

LeanData’s VP of Sales Development, Rob Simmons, uses Kaia, a new real-time conversational intelligence tool from Outreach. “Kaia gives me peace of mind knowing that every moment, note and next step is captured in every meeting. Not only does it help me coach after the fact, but there’s even a proactive element where content cards pop up to help the sales reps in the moment. “Conversational Intelligence is a huge benefit to any sales leader, as it helps us listen to recordings and coach after the fact. Kaia takes it one step further by helping in the moment, when coaching is needed most” says Rob.

Content your reps will need in the moment

Providing the best enablement for talk tracks is not just about preparing ahead of time — or improving after the fact. Reps will be asked questions about competitors, integrations, and pricing on calls. Be sure to give them the answers they need in the moment to drive home the value of your product and make an impression on their prospect. Kaia offers “content cards” that become available on cue during prospect calls. This lets reps respond in real time with confidence to questions like, how does your product compare with your competitors? Or, which tools do you integrate with or have extensions for? You’ll have the same on cue help with pricing cards to answer contract and licensing questions.

What’s next?

When you start building your new talk track, run these insights by your sales reps and collect feedback on what they need to see. Include your reps in the build out to increase their confidence and understanding of the upcoming changes. Get your tools ready and decide which metrics you’ll use to measure the success of a new talk track. For example, Kaia offers on cue coaching and then generates an email summary of the call. Michael Wilde, Account Executive at Honeycomb says it, “allows him to be more focused during meetings as I don’t have to spend my time writing down notes.” He’s able to follow up faster and build stronger relationships with his customers. The introduction of conversational intelligence is an exciting way for enablement teams to support their reps needs. By collecting intelligent insights from every single customer interaction, it’s straightforward to take that information to coach your reps.

How To Strengthen Discovery With Clients In 6 Easy Steps

How To Strengthen Discovery With Clients In 6 Easy Steps

Not converting initial calls to meetings? Are your reps demoing your solution, getting proof
of concepts (POC) placed but not driving sales home? Perhaps you’re a founder or co-
founding CTO solidifying your pitch to potential buyers but not seeing the traction you were
hoping for. Your technology is the most disruptive, innovative and best in class right?

We see this problem among tech companies of all sizes. Clients demoing but not converting.
Clients raising their hand to test the latest technology, you implement a POC and it sits on
the shelf. Why would any of this happen? The client owes you better attention and respect
than that right? WRONG….

“The most common sales area that needs

improvement for vendors is the discovery

process & empathetic listening. Diving into

features/ benefits before fully understanding

the client’s strategic initiatives minimizes the

ability to create an impactful partnership.”


-Amy Looper, Sales Leader & Founder of

Relativity Sells

Let’s dig into how we can engage our clients in a meaningful way and stop boring our clients with stories about our company and our technology. It’s about solving their business issues!

Follow These 6 Steps To Strengthen Your Discovery Process:

1. Set the agenda for your initial discovery call with intention. Ensure that you include the meeting agenda in your calendar invite for easy reference by your client. Most importantly, ensure your agenda brings value.

Example: “The purpose of this call is to learn more about your company’s recent shift into healthcare after the pandemic hit and how you’re adjusting to the influx of business to support. Gaining your feedback on your recent experience growing in this marketplace is helpful so we can best support you in return. If at the end of our call you find our new healthcare management tools of value, a typical next step would be setting up a demo of our solution. Does that sound good to you? Please let me know if there are any other items you’d like to cover during this time.”

2. Show Up Prepared. Press releases, annual reports, online sources such as Crunchbase, Pitchbook, LinkedIn, Twitter are all great ways to understand more about your prospective
clients within the technology industry. The more research you do prior to a call with a
decision-maker the better you’ll have a chance to build rapport, ask questions that they find
insightful instead of the generic sales pitch. Your ultimate goal is to position yourself as an
advisor. Whatever you do, don’t just hop on an in-depth demo without understanding the
client’s business issues which takes me to point #3.

3. Don’t Make Assumptions. You wouldn’t want anyone to assume anything about your business so don’t make an assumption that you understand your potential client’s business.
DO ask them about their vision, their strategic initiatives, confirm info that you may have
seen in a press release but never assume you know their pain because they are similar to another one of your clients. Each client is unique!

4. Focus & Lead With Authentic Questions. Great discovery comes down to the questions
you ask. You’re going to ask more authentic questions if you’re truly dialed into the
conversation and interested in the potential buyer. If the customer mentions that they are
struggling to keep up with the workload in cybersecurity after 2020, you have an
opportunity to empathize and ask them how you can help them. You may be surprised at the
new ways you find to partner with your clients to support them. Need help with empathetic questioning, refer to this list here.

5. Read The Customer & Stay Flexible Without Losing Authority. As noted in
Challenger Selling, there are well over 7 stakeholder personalities involved in every major
technology purchase. Knowing whom you’re talking to, their motives, and reading their
personality is key to keeping the discovery meeting on track. If they are very technical and
are someone who needs to “see it before believing it” then you may just need to give them a
high-level demo while you’re running additional discovery. You may see some buyers not
want to build rapport and just get down to the facts. That’s ok, not everyone is going to be
your happy hour buddy. Staying flexible in working with each personality is critical.

6. Record Discovery Calls. It can be difficult to get all of your discovery questions
answered within the first discovery call. Depending on your sales process, you may have
more than one discovery call with multiple stakeholders. Recording these enables you to
refer back to them for sales detail, use them for market research and practice to improve
future performance. Easy to install apps such as, can transcribe your
Zoom call. Enterprise software like Gong and Chorus gives you the ability to record, make
comments on call recordings for future reference and coaching.

Relativity Sells coaches and provides sales enablement to technology companies around the globe. Relativity’s founder, Amy Looper took her passion for helping technically trained business owners and reps connect with their buyers in a more meaningful way during the sales process. Her coaching and sales enablement services are designed to help vendors understand their competitive positioning, customer’s buyer journey to create meaningful impact, driving long-term revenue and increasing win rates within the sales team. Prior to Relativity Sells, Amy spent 17 years in sales leadership, corporate enterprise sales roles (Fortune 500 cybersecurity, healthcare IT SAAS) where she was awarded 4 President’s Club awards and top sales awards from leading equity firm, Vista Equity. For more information please visit