Career Advice from the Pros: Starting a Sales Career in 2020? Do This

Sales development representative roles have grown 5.7X since 2012, according to LinkedIn’s State of Sales report.

That’s a lot of new people entering sales!

If you’re one of them, that’s both good news and bad: It means sales is growing, but you’re going to have a lot of competition getting started.

So how do you stand out from the crowd? How do you jump-start your sales career and fast-track success?

We reached out to several of our friends — all successful sales pros in a range of roles — to get their input:

Our question: “What is your best advice for anyone starting their sales career in 2020?” I’ll start with my career advice and then share what the others had to say.

Smart Career Advice from 17 Sales Pros

Me, Max Altschuler

VP of Marketing at Outreach
Founder and CEO of Sales Hacker
Co-Founder and Chief Evangelist of SUTRA
Author and Podcast Host

The best advice I have for anyone starting their sales career today is to be patient and cut your teeth. The better the foundation you start your career on, the further and faster you can go.

Start low and optimize for learning, you’ll be way more successful in the long term if you do this. Your 20s are for learning, your 30s are for earning.


Mark Kosoglow

VP of Sales at Outreach

I have a formula that I use on a daily basis:

Effort + Curiosity + Making a connection = Kicking ass.

What does that mean exactly?

It means you have to come in everyday ready to sweat it. If your goal was to send out 100 emails today, and you reach the end of your day with only 93 sent, spend another half-hour in the office and finish your goal.

Be curious about everything. Be curious about your product, and learn everything you can about it. Be curious about your customer, and learn everything you can about them, their needs, and their desires.

Then use what you learned to make a connection between what you know about your product, and what you’ve learned about what your customer needs and wants. If you can do this, you’ll succeed in sales.

Now that may be pretty good advice, but it’s also kind of boring. So, let me give you some more controversial advice to top things off.

Start off by working in telemarketing, and learn how to handle rejection — hearing “no” over and over again, and turning it into a “yes.” That’s something that will always serve you well.

Challenge yourself to have entire conversations where you only ask questions. Try this at a party. Then use this skill with your customers, and put all the focus on them. You’ll learn so much more about them, and they’ll love getting to talk about themselves. Too many sales people want to talk when they should be listening

Before you jump in, make sure you love solving problems, because that’s what we’re really doing here. Our goal isn’t to sell someone something they don’t need. Our goal is to discover what the customer’s root problem is, find a way for them to solve it, and then convince them of that solution. Ideally the solution is your product or service, but even if it isn’t, your goal should be to solve the customers problem. If you don’t enjoy this, then you shouldn’t be in sales.


Collin Cadmus

VP Sales at Aircall
Member of The Revenue Collective

Congratulations! You decided to pursue a career in sales, the best profession in the world. This moment is the start of the rest of your life. The decisions you make now will have an enormous impact on your success or failure in the future.

The best advice I can give to someone looking to get into sales today is to do your due diligence on picking the right company and the right sales leaders to work for.

Startups are great at selling a beautiful story, but don’t forget that over 90% of them fail within the first few years. This means if you launch your sales career with a startup, there’s a good chance that you will fail with them.

You need to be on the defensive to make sure you don’t end up in a bad spot. Vet the startup even more than they vet you. Remember, they are worried about their success more than they’re worried about yours. You’re easily replaceable, and most of them haven’t figured out how to properly support and train new salespeople yet. They have their priorities and you need to have yours.

Ask tough questions.

  • How much cash runway do they have?
  • How many reps have they hired who are now successfully hitting their goals and earning their full OTE?
  • Who are their sales leaders?
  • What experience do they have leading teams to the finish line?
  • What is the exit plan for the startup?
  • What happens if the sales team misses their goal this year?

If they don’t have confident answers to these questions, then look elsewhere. The job market is on your side right now. Take advantage of it, and land yourself at a company that gives you the best chance of long term success.


Trish Bertuzzi

Founder and Ceo of The Bridge Group Inc.
SDR/AE/CSM Evangelist

If you don’t love sales, quit now!

A career in sales can be one of the most rewarding careers, but it’s not easy. If you don’t love the unique challenges of it, then what are you doing here?

Make sure you know what you’re getting yourself into. If you love it, then stay humble and keep pushing forward. Just because you’re successful doesn’t mean you’re the shit.


Mark Roberge

Managing Director at Stage 2 Capital
Professor at Harvard Business School
Former CRO at Hubspot
Best Selling Author

My advice is to invest 5% of your time and money, every month, on personal development. Take that development into your own hands, don’t just rely on your company to do it for you.

First, find a good mentor that is willing to jump on the phone with you once or twice a month to talk about your blockers. It’s important that you find a mentor outside of your company. You will be surprised by how willing people are to help. Find a new sales manager or someone with a few years experience successfully selling. Most will be honored.

Second, set up a peer group to meet monthly. Make sure everyone is in the same boat — new to sales, and maybe even selling in a similar context. Make sure everyone is from different companies so it is a safe place with no risk of politicking. Meet for a drink. Have everyone bring one issue to the meeting, and take turns working on each other’s issues.

I used both of these techniques during my journey at HubSpot, and I learned most of what I know about sales through them.


Amy Volas

Founder and CEO of Avenue Talent Partners

Surround yourself with people who will help you be the best version of yourself.

You are the sum of your parts. Getting bogged down with people who are negative, unsupportive, uncollaborative, and who don’t help you understand your blind spots is detrimental, and will slow you down in the long run.

Surround yourself with the right people, and Immerse yourself into your products and your marketplace. Once you’re doing the right work with the right people, consistently, you’ll pack a serious punch, and set yourself up for success.



Anthony Iannarino

President and Chief Sales Officer at Solutions Staffing
Partner at Iannarino Fullen Group
Keynote Speaker and Workshop Facilitator

Interview potential employers to find one that will give you two things:

1) An excellent, and engaged sales manager. You want someone who cares about ensuring your success, and who will provide you with coaching to help you grow.

2) A modern training program where you will learn how to sell effectively. You want to build the strongest foundation possible at the start.


Aaron Ross

Co-CEO of
Global CEO of Universidade Previsível
Board member of VisualizeROI
Keynote speaker

My best sales advice comes in two parts:

1) Learn how to build your own dashboard, and take charge of the tools and resources you use to help you do your job. Whether you use tools like Outreach, Salesforce, or anything else, don’t rely on other people to get your metrics and dashboards right — learn how to build and personalize them yourself!

This will also force you to figure out the important metrics and gauges that you’ll need to run YOUR own individual “sales business.” You can’t rely on other people to get this right for you.

2) Don’t have any shame or ego about reaching out to anyone and everyone you can for help. Get help from people inside and outside your company. Interview them, sit with them, listen, and learn from as many smart people as you can. Ask questions about sales, your product, your customers, anything you are struggling with, and anything you want to excel in.

Make a list of topics you want to learn about and a list of people you can learn from, and then work down those two lists.


Brooke Bachesta

SDR Manager at Outreach

Be your authentic self.

There are a million different sales methodologies out there, but there’s only one you. Don’t be afraid to experiment with new tactics and test out different talk tracks, but make sure you filter it through your own sales style. Authenticity is so much more inviting than a canned sales pitch, and your prospects with thank you for it.

Stay hungry! This game moves quickly, and If you’re not actively keeping up to date with industry trends, networking in your industry, and learning from people around you, then you’ll get left behind. Invest in yourself.

Own your career! Set big goals for yourself, and push yourself outside of your comfort zone. Learning happens when you’re made to feel uncomfortable — be comfortable with the unknown, ask for new projects, and don’t be afraid to give new ideas a shot and move past them if they don’t work out.


Gaetano DiNardi

Director of Demand Generation at Nextiva
Co-Founder of Musicians in Tech

Be hungry as f*ck, and stay humble.

Get a mentor ASAP, and start embracing a winner’s mindset — refuse to fail, become numb to rejection, and ask for feedback on how to improve from anyone who denies you.

Start building your personal brand early. Become engaged and highly active on LinkedIn. Learn how to be natural on video. Start a content series. Master the art of copywriting, and don’t rely on marketing to do everything for you.

Give 110% with everything you do. Think carefully about your career path, and avoid being short-sighted. Play the long game and prioritize learning and skill building over cash until you are in your 30s.


Justin Welsh

Founder of The Official Justin
Member of The Revenue Collective

Play the long game. Don’t jump at every new opportunity with a $5k or $10k salary bump.

Dig your heels in at a role you enjoy — stay and develop your skills. Practice every day, and refine your craft until you’re the best at your company.

Shortcuts in sales are a quick way to go nowhere. You’ll accelerate your career by going long, not by taking shortcuts.


John Barrows

CEO of JBarrows Sales Training

Try everything. There is no right or wrong approach to most sales (as long as you are being ethical). It’s all about trying different methods to see what works for you.

If you’re conscious about trying different approaches, you’ll start to identify the ones that work and the ones that don’t for you.

The way I do this now is by A/B split testing everything. I Identify a challenge (getting through gatekeepers, dealing with a pricing objection, getting to power), and then I identify two different approaches to solving that challenge.

I’ll use one approach 20–30 times, and then use the other approach 20–30 times. Then I go through the numbers and figure out which one yielded a more positive outcome. By split testing everything you do you’ll figure out what works best for you and improve a lot faster.

If I could go back in time and give my 22-year-old self advice when I was getting into sales, it would be to do A/B split testing on everything.


Jill Rowley

Member Board of Directors at Affinio
Partner at Stage 2 Capital
Partner at Sales for Life

Spend some time making sure that you are interesting to your buyers, and be interested in them too.

Spend time studying who your customers are, what they want, and then make sure you are the kind of person who will attract them, the kind of person they want to talk to.



Jake Dunlap

CEO at Skaled Consulting and Skaled Media
LP at Stage 2 Capital

Start learning sales technology now.

The reps who will win in the future will be the ones who use tech to be more efficient, so they can spend more of their time working with customers and on accounts.


Josh Allen

Chief Revenue Officer at Drift

Before getting into sales, you need to make sure you understand what sales is and why you want to be there.

If the only reason you want to be in sales is to make money, then you’re going into it for the wrong reasons, and it likely won’t be a good fit.

If you’re here because you love the challenge of it, the competition, and the puzzle of human psychology, then you’ll probably go far in sales.

One of the great things and one of the tough things about sales is that it’s almost entirely performance based. So, don’t be impatient.

Cut your teeth, take the time, and earn it. Don’t expect anything to be handed to you in sales. You have to earn it. But if you do, you’ll find yourself moving up and succeeding.

This may take time, which is why you shouldn’t be in this job unless you love it.

Another tip I have is that you need to be able to meet the customer where they are, and adapt to any form of communication they want. The biggest difference between sales today and sales a decade ago is how we communicate with the customer. In today’s world, the customer chooses the medium of that conversation.

The top performers in sales have a high emotional intelligence, and can feel out where the customer wants to communicate, adapt to that, and meet them there.


Sangram Vajre

Co-founder at Terminus
Author and Podcast Host

Start creating content now. Become an expert in the industry you want to work in. It’s no longer just a “marketing” thing to do.

Remember: consistency creates massive outcomes.


Tiffani Bova

Growth & Innovation Evangelist at Salesforce
Bestselling Author
Podcast Host

I changed jobs a lot early in my sales career, so I learned a thing or two about getting started. There are a few tips I want to highlight.

Become who you aspire to be — You should push yourself beyond your comfort zone. Look at who you want to be in 3–5 years. That could be a sales manager, a leader, an executive.

In order to reach that goal, you have to try new things and use every job as an opportunity to better yourself and learn. Become a student of your future profession.

Treat the customer network with respect — With each new sales job, you bring your network of customers with you (as long as you aren’t tied to a non-compete, of course). That Rolodex of clients is part of the value you bring to your new employer. Care for that list, and cultivate those relationships. Don’t overuse them or abuse them, because they are one of the most valuable resources you have.

Introduce yourself to the people who will be supporting you — Sales is a team sport. There are so many parts of the company that support you every day, and it’s very important that you get to know those people. These are people like:

  • Finance – who helps you with pricing and turning around complex quotes faster shipping
  • Logistics – when you need a rush-delivery handled
  • Customer services – who your customers will often talk to

Figure out who those people are and establish a relationship with them. Otherwise, when you really need help, you won’t know where to go.

Last but not least, as sales people, our careers are really quite simple. It doesn’t matter if you do all the things I suggested above or anything anyone else has suggested — if you don’t hit your numbers, you will be faced with finding a new job somewhere else. So go sell something!


Bottom Line

If you’re still reading this, chances are, you’ve already got a head start on a great career in sales. You’ve started down a path to one of the most rewarding (and challenging) careers you could have chosen. 

I think you’ve made the right choice. There is no better time than now to get started in sales, but it’s up to you to make it happen.

Get to work, take these tips to heart, and like Tiffani Bova said, “Go sell something.”

With some work, some time, and a little bit of luck, you’ll soon be one of the people on this list giving career advice to the next generation of sales people.

Max Altschuler is currently the VP of Sales Engagement at Outreach. He is as passionate about the sales profession as they come. He created the premier B2B Sales media company for all things sales innovation, Sales Hacker, and ramped them up to over 150,000 monthly visitors before joining Outreach through acquisition. At Outreach, he leads all things marketing, along with the continued evolution of the Sales Hacker community. Max is a highly regarded sales thought-leader published by Forbes, Time, Inc, Harvard Business Review, and Quora. He wrote the book on modern sales called Hacking Sales: The Playbook For Building A High Velocity Sales Machine, which was published by Wiley.

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