Whether it be ugly ducklings, misfit toys, or square pegs in round holes, some things just don't fit in — but in most cases, it's purely situational.

Ugly ducklings can turn into swans. Misfit toys had an entire island to themselves. And not all holes are round. Sometimes fitting in just means shifting circumstances — and that principle applies to different brands of sales.

Sometimes sales professionals currently working outside sales aren't cut out for it. Maybe, it doesn't play to their strengths. Maybe, it's too physically exhausting. Maybe, they flat-out don't like it. That doesn't mean they can't be effective salespeople — it just means they need to change things up.

If you find yourself in a position like that, you might want to consider transitioning from outside to inside sales. And to help your case, we reached out to HubSpot experts who made that jump for their input on what mastering inside sales entails.

[New Data] The 2021 Sales Enablement Report

1. Be the change you want to be.

Sharen Murnaghan, HubSpot Solutions Partner Growth Specialist, about her experience transitioning from inside to outside sales, the first bit of advice she offered had to do with taking initiative.

After starting her career in the print industry, Murnaghan decided she wanted to be a digital salesperson, but lacked experience in the field. According to her, "[She] needed to skill up in digital." She borrowed money from a credit union and took night classes to get a post-grad diploma in digital marketing.

She understood what she wanted out of her career and took on the legwork necessary to make that happen. The kind of ambition she demonstrated would hold weight in any field but is particularly valuable in inside sales. If you want to make the shift from outside to inside, that burden falls on you — above all else.

2. Build on top of the process.

Murnaghan also advised any aspiring inside sales reps to unlearn some of the more fundamentally ingrained lessons of their previous experience. Outside sales is a different game, so you need to embrace some different rules if you want to make a seamless transition.

In her case, she "focused onembracing all that [she] could learn." She read books, asked questions, shadowed other high flyers, and scheduled meetings with top executives — all while setting goals and establishing firm plans to achieve them.

Through strategy, humility, and tremendous effort, Sharen bolstered her inside sales skill set and accrued the necessary knowledge to assume her new position with tact and momentum — providing a lesson that every aspiring inside sales rep should heed.

3. Really care.

Finally, Sharen advised reps looking to transition from outside to inside sales sincerely care about their colleagues, customers, and company. By her account, inside reps should "always be present...I try to always be there to help my colleagues — primarily because they were there to help me — it's good to pass these things on."

She suggests that the best inside sales reps are always interested and sharing. According to her, if you can commit to those aspects of the job, you'll be in a solid position to seamlessly transition between the two schools of sales.

4. Immediately share your expertise and LinkedIn profile to promote credibility.

HubSpot Principal Account Executive Kristen Kelley also provided some sage advice for sales reps looking to make the shift between outside and inside sales. Her first piece of advice had to do with establishing trust and authority with prospects.

One of the tactics she cited was particularly straightforward — immediately share your expertise and LinkedIn profile to promote credibility. According to her, "Your buyer needs to understand that you’re a real human being who can add value to the evaluation as opposed to a call center rep they’ll never speak with again."

5. Always be yourself!  

Kelley also stressed the importance of sincerity, individuality, and authenticity in inside sales. She advises all aspiring inside sales reps to be themselves around prospects. She says, "Robotic conversations are a bore and a drag for everyone involved — just keep it real!"

There's a human element to inside sales that you can't gloss over or push down. When it comes down to it, prospects are people that want to hear from other people. Ditch the rigidity and excessive formality if you want to hack it in inside sales.

6. Explain the typical process for sales evaluations from beginning to end, including your expectations of your prospect.

Inside sales is a two-way street. There needs to be mutual investment and understanding if there's going to be a successful relationship on the other side of the deal.

Kelley touched on the importance of this point by saying, "Make your prospects aware that if you’re investing time with them, then they need to be accountable to you as well — even if accountability means telling you it’s not the right fit."

7. Turn on your video during conference calls.

Kelley had another simple, straightforward point rooted in adding a personal edge to your inside sales game — turning your video on over conference calls. Let your prospects see that beautiful mug of yours. According to her, "It will engage both visual and auditory senses, promoting a deeper relationship and engendering trust."

8. Always schedule a reconnect before ending a call — even if it’s just a placeholder that can be adjusted at a future date.

You want to keep a grip and a pulse on any engagement with prospects. One of the better ways inside salespeople can do that is through scheduling reconnects before the ends of their calls. As Kelley puts it, "Reconnects help you maintain control of the process. Otherwise, you’ll waste time and energy chasing your prospect on next steps."

9. Consider creating a collaborative, mutual action plan in a shared document to collaborate on next steps and ownership of next steps.

Another way to foster collaboration and accountability with your prospects is through creating mutually constructed, readily accessible action plans — ones that outline every step of the process with dates and owners, all the way to your close date.

As Kelley puts it, "These plans are especially useful in complicated sales evaluations with lots of stakeholders, but they can also quickly reveal someone’s level of commitment in any type of evaluation."

10. Do a temperature check to understand your prospect’s interest level.

The best inside sales reps can read their prospects. And sometimes getting there means explicitly asking them how they're feeling. Kelley recommends reps gauge prospects' interest by having them rate it on a one to 10 scale.

She says, "Ask them 'on a scale of one to 10, with 10 being you want to purchase right away and one being you never want to talk to us again — where are you right now?'

"If it’s 10, get them started.  If it’s over five, ask them what it will take to get them to a 10. If it’s under five, discuss whether it makes sense to continue the conversation."

According to her, "This exercise is so useful to gauge interest and it works so well, prospects love it! Everyone likes sharing their opinion."

11. Make it easy for them to exit.

Kelley refers to this point as a "HubSpot value" but stresses that it's valuable in any sales process — no matter if it's inside or outside sales.

She suggests that you "let [prospects] know that if at any time you determine that your solution isn’t the right fit for them, you will tell them immediately." She also says it's best practice to "encourage them to do the same. Ask them if they will tell you if they have any doubts or concerns."

12. Break up if necessary.

In inside sales, sometimes you're better off cutting and running — sunk costs and all that. Kelley says, "If your prospect is ghosting, always remember that there’s more fish in the sea and send them a professional break up email. If they’re really interested, they’ll respond. If not, you just cleared your calendar for valid prospects."

She tied this point back to her policy on authenticity, "Always keep it real — particularly with yourself — by maintaining a clean, legitimate pipeline. Take back your power and create closure with a breakup, one of the most useful tools in sales!"

HubSpot Sales Director Dan Tyre's Four-Point Framework for Aspiring Inside Salespeople

HubSpot Sales Director Dan Tyre offered some insight about his personal experience shifting from outside to inside sales.

He says, "Before I joined HubSpot in 2007, I spent 30 years leading outside sales teams to generate business. Back in the outside selling era, the salespeople got all the budget, visibility, and glory.

"Sales was the king and marketing was in the doghouse — either they didn't create enough leads or they created too many (no matter what, we constantly complained about their performance.)

"Marketing created the brand and generated leads, and the outside sales team took all those leads, qualified them, set prospects up for a product demo, answered objections, and brought people to a closing sequence — a solid 95% of the sales process.

"When I joined HubSpot, the process was different — inbound leads just appeared and were significantly more engaged, interested, and sales-ready. Therefore there were different skills involved:

  • Preparation: In the old outside days, you could show up and do 'discovery' ask questions about the person and company — inside salespeople do their research ahead of time.
  • Pace: Also in the old days, you did two or three sales calls a day because you had to drive from one prospect to the next. Today you can do six in a day! But you have to move quickly and have good technology. What I learned about pace is that I needed to be set up for my full day before I started and I needed good tech automation like sequences and an easy-to-use CRM to make it easy.
  • Velocity: You have to get to the point faster. In the outside days, we spent a lot of time building the relationship to potentially do business down the road. In the inside world, the road is today. People want to move fast, and they want you to do all the work.
  • Consistent contact: In the outside world, it was 'buyer beware'. In the inside process, it's 'seller beware' because you have to stay involved with the prospect over the life of the engagement to build high trust. I learned to check in with my clients four or so times a year to make sure things worked."

As you can see, transitioning from outside to inside sales can be tough — a process with plenty of balls in the air — so that begs the question, "Why do it?"

So what's the appeal here? Why would you ever want to apply the advice our experts provided? What's the point of transitioning between these two brands of sales? Well, we asked HubSpot Partner Sales Enablement Lead David Weinhaus to speak to the benefits of making the shift, and he had this to say:

"Transitioning from outside to inside sales has been a blessing. Sure, I miss the excitement of traveling — going from belt buckle to belt buckle, seeing the physical space of those I'm selling to, and entertaining.

"But the advantages of inside selling are so much greater. For one, field selling is physically demanding. I remember when I sold in the field, my dream was that every business I drove by had a light bulb above it.

"When it was turned on, it would magically indicate that they had a pressing need for my services. I wouldn't have to waste countless hours traveling, especially for sales calls where the prospect really had no need.

"What I've come to learn is that inbound marketing plus inside selling does exactly that. Marketing finds leads that have the light bulb turned on, as evidenced through their online behavior. And then inside sales calls on them.

"When a lead has demonstrated a pressing need, you don't have to charm and entertain them in person. In fact, the phone and Zoom work just as well — oftentimes better. And it can all be done from your desk close to home so you can spend less time traveling and more time on other priorities."

Inside sales isn't for everyone. If you're happy working in field sales, there's nothing wrong with that. But if you're an outside salesperson having a hard time — and the benefits David described speak to you and your interests — you might want to look into making the shift and heed the advice listed here.

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 2021 Sales Enablement Report

Originally published Feb 3, 2021 2:15:00 PM, updated February 04 2021