What Kind of Sales Role is Best for Me?

If you’ve ever found yourself asking this question, don’t worry, you’re not alone.

Personally I’ve asked myself this a number of time. For most of my career I’ve been part of and managed Inside Sales teams. It’s been a good fit for me compared to my time in outside sales. Every time I think about returning to outside sales I remember all the perks and get dreamy about it before all the reasons I left outside sales start to creep up in my mind.

A lot of reps are curious about how the other half lives. It’s smart to be a bit curious about what else is out there.

Here are the most important things you should consider as you figure out what your next, or even first, ideal sales role would be.

First and foremost ask yourself, where are you in your sales career? This is crucial in understanding what options are open to you at this exact stage in your career.

Early Career

If this is your first Sales role you’re going to have to take a job where you do a ton of prospecting. It doesn’t matter if you get hired as someone who closes business or set appointments for the Sales team who closes business, you’re going to do tons of prospecting.

In my first Sales role I was responsible for developing and managing a geographic territory. What that meant was on day one I had exactly zero customers and zero leads. I had no professional network, either. The only was I was going to find new business was to research my territory for companies in our target industries and prospect into them.

The roles I interviewed for early in my career all had the same theme, whether the role was selling insurance, advertising, professional services, or borderline commodity products. Everyone told me to be ready to prospect a lot.

For most of the past nine years I’ve been hiring entry-level Inside Sales reps. The role? Prospecting. Appointment setting. I’ve overseen reps who made over 100 calls every single day to mainly cold leads. Two of my teams did highly strategic enterprise account development, which involves a lot of figuring out who you need to talk to and what they’d potentially be interested in. All of them spent most of their day prospecting into accounts.

I can tell you firsthand that it’s not glamorous work at all.

Why do companies start reps out making tons of prospecting activities? A few key reasons.

First off, companies want to weed out the people who want to succeed from the reps who want it to be easy. Sales isn’t easy, no matter how long you do it. If you’re not willing to prospect early on in your career then how are you going to be successful later on?

Because reason number two is that yes, odds are you will have to prospect into accounts for the rest of your sales career. No matter how good you get, no matter how cushy the company is, there are very few sales roles that involve zero prospecting.

Inside vs Outside Sales

Trying to describe the difference between inside and outside sales is difficult because there is no hard and fast set of rules. There are a few general advantages to each.

Outside sales reps typically have a home office and are constantly on the road driving. Your employer may provide you with everything you need to do the job, and they may not provide you with anything other than a territory and a quota.

Some reps have huge geographic territories and are constantly flying to meet with clients and prospects.

Most of your day you’re out meeting or trying to meet with people. There is a lot of flexibility in this type of role. If you need structure or struggle with planning, odds are you will fail in an outside sales role because your employer is going to expect you to be completely self sufficient and organized.

The role can also be lonely because most of your conversations are over the phone. If you live close enough to the office you’ll likely have a weekly or monthly meeting with the whole team there. It’s not all lonely, though. Your focus is meeting with prospects and clients, so you will have a lot of interaction with them.

When you’re an inside sales rep you go to work in an office. The company provides you with everything you need to do your job, just like anyone else in the office.

It’s a far more structured environment because your boss sits near you and everyone is working similar hours with similar territories. The sales team sits all around you as well. Have a question? Walk up to someone’s desk. It’s a far simpler set up.

This also means it’s hard to find a quiet place to make calls. You’re going to have most of your sales conversations in the middle of the sales floor, where everyone else sits and has their sales conversations. The sales floor can get very loud.

Working successfully in an inside sales environment requires a different kind of discipline to being an outside sales rep. Unlike an outside sales rep you wake up, get ready for work, then commute to work before starting your day. It’s easy to get distracted in side conversations. There’s always something going on in the office, whether it’s sales related or not.


If there’s one thing I can’t stress enough, it’s to make sure you sell something you think is interesting, useful, and that you’d sell to your own family if they were your prospect.

Keep that in mind as you consider what industries you’d like to sell in and sell to.

Most industries are fairly vague. Here’s a short list of industries: technology, industrial supplies, professional services, logistics, manufacturing, marketing and advertising, financial services, food and beverage, insurance, and transportation.

Can you name at least one company in each industry? I bet you can.

Now, can you name one more company in each industry that doesn’t compete with the first company you named?

How about a company that sells to each of the companies you named from all of the other industries?

Picking an industry is more complicated than merely picking what you sell, it’s also picking how you sell and who you sell to. All of those factors are going to affect your job. Let’s talk about each one a little more.

When you think about the industry you want to work in, you have to consider both what you sell and who you sell to. Let’s take healthcare for example. What do you want to sell in healthcare? Do you want to sell hospital supplies, medical devices, or the software the facility depends on to track their patients? All three are drastically different in sales process, who you sell to, and what your work is going to look like.

Sales process is extremely important to consider. There are tons of short sales cycle companies in almost every industry, and many of those same industries have products and services that an experienced enterprise sales professional navigates over a twelve month buying process.

Early on in your career you will be selling in shorter sales cycles, so don’t worry about which is right for you yet. You will have a chance to figure out what suits you best long-term once you’re proven you can sell.

Who you sell to is crucial. If you ever want to change industries, knowing the prospect you sell to is an easy way to make a case to a new employer that you’re going to be able to do well selling for them.

Trust me, it easier to go from selling professional services to marketers one day to offering marketing software the next than it is to go from selling software to marketers one day and then selling software to IT professionals the next. There’s a huge difference between marketers and IT professionals. You’ll have an easier time learning a new product than learning a new customer.

Focus on who you sell to. It’s just as important as selling something you like and would sell to your friends and family if they were the prospect. You can figure everything else out down the road.

Figuring out the kind of company you should sell for

One of the biggest challenges is figuring out the size company you should work for. I’ve worked for big national companies, in 100+ employee startups, in an established small company, and as a startup cofounder. They’re all dramatically different in their own ways.

What I recommend doing is to think about what kind of experience you want in your next role and work backwards from there. Key questions to ask yourself:

How much training, coaching, and mentoring are you looking for? What are the odds you’ll be successful without these resources?

How much structure and guidance do you want? Are you comfortable with ambiguity?

How fast do you want to advance your career? Are you more focused on short-term advancement or long-term career stability?

How much risk are you willing to take? What it mean to you if you don’t succeed in the job?

How much money do you want to make and how quickly do you want to hit that number?

Prioritize each of these. Why? Because there’s no sales role that has extensive training and coaching, tons of structure and support, a super fast career path, has a huge paycheck, and is extremely stable and secure. None. You’re going to have to pick what’s most important to you based on where you personally are in your career, what you want to achieve, how quickly you want to get there, and how much risk you’re willing to take on to make that happen.

Your priorities are going to change over time, which is perfectly normal.

Early in my career I was looking for fast career advancement and I was willing to take on risk. I had some amazing experiences, but I also found out firsthand what happens when you bet your immediate future on a startup and that company goes under. Personally, I’m glad I did that when it made sense for my career.

After the startup went under I focused heavily on skills development to set myself up for the next phase of my career. More recently I’ve been more focused on roles where I can see myself in them for at least 2-3 years. I’m sure someday that will change again and I might move back into a bigger risk/reward situation.

It’s all relative to what you want to achieve.

Hunting, Farming, Inbound, Outbound, Upsell, New Logo – What’s the Right Fit?

One crucial area reps don’t always consider early on is the kind of sales work they’ll be doing and how that will impact their future.

What do I mean by that?

Sales roles are not all the same. In fact, there are many reps with the exact same title with similar responsibilities, yet the actual roles themselves are significantly different in specific ways. These differences matter, both for you now and for you down the line.

The most important question to ask is, who are you selling to?

True sales roles will focus on selling to new customers. Sometimes it will include selling new products into existing customers, or selling into other business units in existing customers. You may be responsible for keeping your customers happy and get paid commissions if they continue to do business with you.

All other things equal, the biggest paychecks go to the sales reps who solely source new business. It’s the hardest sales role, hands down. You spend your days either trying to earn business by displacing a current vendor, or, if you really want a challenge, you do so by trying to earn business by showing your prospect they need to buy something they’ve never bought before.

Reps who close new business are faced with the task of changing someone’s mind completely. It’s a massive challenge, one that most new reps don’t appreciate until they’re trying to wrap up their first deal.

If you’re selling to existing customers – and only existing customers – you’re working on the client side of the house. Odds are you won’t be able to move to the new business sales team, because your job is nothing like their’s. Be cautious moving to a client facing role for too long if your goal is to close new business.

Now, the second most important question to ask is, where are your leads coming from?

Some sales reps do not source any of their leads as their focus is 100% on taking meetings from an inside sales (SDR/BDR/LG/etc) team and turning them into opportunities whenever possible. These are great organizations to get into as an SDR as they’ll often have a career path into a closing role. Plus once you’ve been promoted you’ll spend your days developing deals instead of chasing prospects for a first meeting.

For the reps who have to set up meetings, there are three kinds of leads: cold, warm, and BOFU (bottom of the funnel).

Cold leads are exactly what you think they are, prospects who have shown little or no clear signs of interest up to this point. It’s your job to generate enough initial curiosity and value that they’ll take an introductory meeting.

Warm leads are typically people who’ve requested some information from your company but have not requested a demo specifically. This could mean they downloaded content from your website, replied to a direct mail or direct response piece, or even emailed your company looking for some info. You have their contact information, yes. You do not usually have a perfect idea of their intentions and if they’re a good prospect or not.

BOFU leads are prospects who have raised their hands and requested a demo. These are the easiest leads to follow up on, by far.

Much like above, the most valuable and hardest skill set is developing cold leads.

There’s a shift happening now that’s segmenting reps who source cold leads from reps who source warm/BOFU leads as the difference between sales and client services. Companies are already making that a clear line in terms of your career potential.

My two cents on this: I’m all for this separation. The skills you develop chasing cold leads is lightyears beyond the skills you develop with warm leads. Why? Because you have to learn how to get the prospect to speak with you without a guaranteed conversation starter. I’ve seen a number of reps do great with warm leads and struggle with cold leads for this very reason.

One thing to consider for your career. If you realize you’re not a cold leads, new business, hunt and close deals kind of rep, then good for you. There are a number of career options still open to you that have sales aspects to them. On the flip side if you realize that hunting is for you make sure you take a hunting role. It’s much easier to go from closing new business to working with existing clients and warm leads than to go from client facing to hunting. Many companies will not take that risk because they know you lack certain base level skills that are essential to hunting and closing new business.

Sales Cycle: Transactional, Short, or Enterprise

I put this last because in a certain way it’s the easiest aspect of a sales job to figure out.

Start out by asking yourself what parts of the sales process you like the most. Are you someone who’s always looking for a way to build relationships, consensus, and get more people involved in a deal that seems to take forever to finally close? Do you prefer to be able to close prospects in one call and notch another deal on the board?

You may not feel strongly about one or the other. That’s okay. There is a wide spectrum of sales roles and you fit somewhere on it.

The key here is to always ask yourself what excites you about sales. What do you wake up and look forward to when you’re trying to advance and close a deal?

Your ideal role won’t necessarily stay the same. Over time you might find yourself leaning one way or another. You might start to want to spend more time developing deals. You may realize you need to constantly be closing deals so you can move onto the next one.

Reps who love closing deal after deal should look for sales roles with shorter sales cycles. This can be as short as one call. If you’ve never done that, think about the rollercoaster of getting a prospect to buy-in strong enough to say “yes” at the end of your first call. It’s quite a thrill!

Enterprise reps spend their days working on major accounts, meeting new people, finding their champion or mobilizer, building consensus, and steadily working towards a deal that often takes 6, 9, 12, or even 18 months. Some teams work on deals that take years before a decision is made. These deals are often hundreds of thousands of dollars, if not millions. Think about the huge sense of achievement you’d feel after working on a single deal for nearly a year to finally close it!

If neither of those sounds perfect, there are a lot of in-between sales roles. Many products need a little more time and effort to close than a transactional deal, yet don’t involve the complex development and buy-in that an enterprise deal would take.

Whatever path you go down, stay true to yourself and put yourself in the best position to succeed!

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