30 Outside Sales Tips To Help You Win More Opportunities in 2023

photo of outside sales reps talking about an opportunity

Feeling overwhelmed by the infinite options for growing your pipeline? You’re not the only outside sales rep feeling that way.

This article doesn’t list every outside sales strategy under the sun.

Instead, it lists the tactics our clients use at Veloxy. These are tactics that have helped outside sales professionals grow their pipeline by 300% in one month.

In other words, they’re proven to work.

Here is the list of our Outside Sales Gurus’ Top 25 Secrets (NOTE: We’ll be using field sales and outside sales interchangeably):

Don’t forget: Read the largest outside sales guide on the planet!

1. Know your product

Whereas inside sales reps need to speak intelligently about their products, outside sales reps also need to know how best to use their products, their industrial applications, and in some cases the products’ intricate engineering.

This is why outside sales teams can comprise of product managers, industry experts, and former end-users of the products. It’s also why an outside sales salary is typically much higher than their inside sales counterparts.

In addition to knowing about the product, outside sales reps are best suited to gather intelligence on product improvements. From long-lasting client relationships to face-to-face meetings, field reps can make all the difference in innovation by continually supporting customer needs.

This is one of the toughest sales jobs there is—strong-minded salespeople need only apply!

photo of outside sales rep demoing product

2. Aim for the moon with targets and quotas

In the words of the famous Michelangelo, the greater danger doesn’t lie in aiming too high and falling short. Instead, we hurt ourselves more when we aim too low and actually achieve the mark.

Here’s a mentality that top-tier outside sales gurus have. If you’ve been meeting quota attainment for the past few months in a row, then you’re clearly underplaying your real potential.

To be the GOAT of the sales team, the experts advise setting sales targets that actually scare you. Scarier sales goals will not only force you to plan proactively, they literally scare you into action.

The sales goals will motivate you to gather more quality data and knowledge as you strive to hit these seemingly impossible numbers. But once you achieve them, then you’ll continually challenge yourself and elevate your standard as your own competition, and exceed quota attainment.

3. Customers come first

While you’re busy trying to meet your sales quota, remember to value the customer more than anything else. Inside or outside, all the best salespeople know just how important it is to support the customer’s needs. And while you can always push a product for the sake of selling it, you’ll only sell it once.

But if you can win a customer’s loyalty and focus on what they really need in a product, then you’ll be creating customers for life. Offer them suggestions from your portfolio that match their requisition.

And in case you don’t know all your stuff or lack knowledge about a particular aspect of the product, make sure you come prepared with relevant information or ask someone on your sales team.

Don’t be afraid of being proactive and fetching intel from different departments before proceeding with the sale. If you take care of the customers, then the sales and money will follow you as opposed to the other way round.

customer meeting with outside reps

4. Send a quote ASAP

Did you know that customers feel more urgency to make a decision when they have a sales quote in hand?

They may have a written statement with the price, variants, product details, services, and other information required to complete the transaction. But more often than not, customers won’t come asking for a quote. You have to give them the estimate when you feel the time is right or if the sales inquiry comes in.

Whether it’s through a call or email, make sure the lead gets their sales quote. Don’t forget to add a number or email address where the lead can reach you with regards to the estimate. The sales quote will be just the first of many documents to follow, so you might as well get on with it early enough.

5. Embrace sales technology and analytics

Sales technology is among the biggest facilitators that help managers solve the biggest problems that come with outside sales. This especially applies to CRM and managing customer data, and quota attainment.

Remember – data is good, but sales analytics make it great. A lot of sales reps end up competing on who sold the most or what product is selling faster. However, salespeople tend to miss the bigger picture.

Sales analytics help you and your sales team know how the sales graph is mapped out and what aspects need to be fixed. Maybe you’re selling the right products to the wrong audience in the wrong market.

photo of sales tech stack

6. Find an outside sales mentor or protege

While collaborative selling is a hot topic right now, the old-fashioned practice of finding a mentor (or a protege) has fallen by the wayside.

The enormous digital footprint of today’s outside sales representatives has inspired lonely self-improvement efforts such as attending online seminars and reading books written by 1 of 1,000+ sales icons. Use LinkedIn to find a seasoned outside sales veteran in your area or network, or simply reach out to an in-house colleague with great sales experience. More times than not they’ll appreciate and invest in the opportunity to help you.

While having an outside sales mentor is critical, having an outside sales protege can be just as beneficial to your career. When helping a sales amateur or even a college student, your awareness with regard to accountability will be huge, so you’ll subconsciously drive yourself to stay ahead of outside sales trends and never leave your protege behind. The best way to find a protege is to contact your local business schools or alumni.

Now is the best time to schedule video calls while we’re stuck in the remote sales world.

7. Stay organized with sales automation

Stop me if you’ve heard this before. “Make sure you organize your efforts at the end of the day!” After a quick nod and hidden eye-roll, you think to yourself “I don’t have time, I’m a salesperson, I need to sell!”

It’s all too common today to spend one to two hours every day on non-selling activities. That’s right, the activities that do not generate revenue are taking up a significant portion of your day. And even worse, if your day runs long, your partner will not be happy with you spending more time with your CRM than with them.

Luckily for you, there is field sales technology that can automate your calendar and follow-up. In addition to Sales Artificial Intelligence that prompts you with optimal times to reach out to a lead, it can also extract key dates and names from emails and automatically add them to your customer relationship management software.

photo representing a sales manager deploying salesforce automation

8. Use GPS prospect discovery

Tools like Veloxy Mobile can help you find new leads when you’re out in the field. Whether you’re walking into a client meeting, or sitting in your local Starbucks, it’s as simple as one-click on your phone to find a closeby lead and download their information.

As I shared earlier, it’s wise to remain knowledgeable about your products. It’s even wiser to demonstrate your knowledge of the industry. Stopping into prospective companies and dropping off a business card and info sheet shows that you’re aware of their business, their executive staff, and based on the content, you’re probably aware of their pain points and newsworthy activity.

If you’re using Veloxy, you can also do all of this new prospect downloading from the comfort of our web portal. Be hyper-efficient by planning your route and stop-ins ahead of time!

9. Use account-based selling in the field

In the old days, field sales reps only had the names and numbers of a few select contacts. Now, with the ever-expanding presence of data, we can use tools like ZoomInfo to quickly uncover Org Charts and learn of the latest personnel promotions.

While inside sales has to leverage account-based selling virtually, field reps can follow up on business intelligence in person. From dropping off a care package to congratulate the new CMO on their promotion, to confidently asking to speak with another contact with a similar buying power, account-based selling was seemingly made for the outside sales model.

If you have your smartphone with you during a visit, you can use Veloxy’s mobile app to access an eagle’s eye view of the decision-makers, team environment, their past and present activity, and their latest social media post.

10. Eliminate non-selling activity on the road

Picture this. You’re driving to a client meeting downtown, and your phone buzzes twice. One is an email from a lead, and the other is a phone call from an opportunity. As you pull off to the side of the road, you answer the phone and begin discussing your proposal while scrambling for a pen and paper. You frantically start writing a note to yourself on your smartphone, and as the call ends, you realize you have three minutes to respond to the prospect’s email.

This is the sales process struggle that outside sales reps have been living with for 20+ years. Thanks to the growing development of new smartphone apps and integrations for our most essential business technology, there’s now a series of apps to eliminate non-selling activities like record keeping, lead creation, CRM field updating, and more.

While having a personal assistant back at your office is nice, having an AI (artificial intelligence) personal assistant on your phone is even better. Studies at Veloxy have shown that outside sales reps who use Veloxy to eliminate non-selling activity save 1-2 hours every day and $12,500 every year.

Eliminating non-selling activity is a sales strategy that will quickly deliver ROI!

If the average sales rep is expected to miss their quota, and they spend over 60% of their time on non-selling activity, how are they supposed to satisfy quota AND CX/CSAT?

11. Enable yourself to sell from anywhere, any time

While having GPS and sales automation apps running on your mobile phone, you as an outside sales representative are never in the same environment every day. Today you’re in a conference hall. Tomorrow you’re driving from one office park to another. And two days from now you’re going to be in a hotel without your laptop. What is an outside sales rep to do!

As we continue to recommend sales technology to outside sales reps, we also like to promote sales technology consolidation (few solutions, greater productivity) and flexibility. There are truly remarkable sales tools out there, but some are landlocked on a particular device (desktop/laptop, smartphone, tablet, etc.).

When you’re demoing sales technology, always ask about accessibility. It’s commonly overlooked, and that’s why we quickly deployed Veloxy Sales AI as an inbox extension (Outlook and Gmail), smartphone app (Droid and Apple), and a web portal. We even had an Apple Watch app for a while!

12. Become a storyteller

Similar to knowing your product, you also need to know case studies inside and out.

Years ago I was working hard to generate leads for an electronic signature software. I noticed that there was a good portion of male prospects that lived within 100 miles of a popular football team. I recalled that one of the case studies was for this very football organization, and they had just signed a superstar quarterback to a multimillion-dollar deal. You guessed it—he signed the contract with the electronic signature software!

I generated dozens of meetings from that tailored approach, but the leads told me it was more than that—it was how I told the story. Humans have been telling stories for thousands of years. Stories are hypnotic, and they’re extremely effective at conveying a message. Be sure you can tell stories confidently to your leads and customers.

13. Deliver content in person

Inside sales reps enjoy using tools like Sendoso to automagically deliver direct mail to their leads. However, inside sales reps are jealous of outside sales reps because they can deliver content in person, and this can have a powerful impact on shortening sales cycles.

We’ve all been there. Our mail is dropped off at our desk, and we flip through it all like a child on Christmas morning, hoping there’s a big prize. Although in a business environment it’s mostly bills and invitations, a piece of marketing content with a fluorescent post-it note works wonders for getting callbacks! ‘Let’s grab lunch. Larry 123-456-7890‘.

If you offer your lead a free lunch, you can rest assure they’re going to read the piece of content that you dropped off.

14. Use data-driven insights to improve engagement

We’ve all been there. We have two meetings in a city one day, one in the morning and one in the afternoon. Looking at the calendar, we see there are 2-3 hours of open time. What if you knew which prospects and clients in close proximity typically open their emails or answer their phones in that same 2-3 hour window?

That’s right—you’d most likely find them available when you swing by to say hello. These are data-driven insights that many sales tools are delivering to outside sales reps these days. The most powerful data-driven insights are automatically discovered by sales artificial intelligence, and even better, they are also automatically delivered to outside sales reps based on time or geolocation.

Inside sales reps have been using similar insights as a boom to their sales performance, and there’s no better time than now for outside sales reps to take advantage and ride the wave to more deals! Make sure this is one of your top 2023 sales strategies.

Did you know that 81% of B2B buyers expect sales reps to understand their needs and expectations—this includes when to send an email and when to call them.

15. Collaborate with inside sales reps

What’s your favorite war movie? There are so many good ones. Saving Private Ryan. We Were Soldiers.

In each of these movies, there are scenes where the men on the battlefield radio back to base for commands, for reinforcements, or to strategize the next counterattack. Outside sales reps can learn a lot from such movies because one of the most trending sales process these days is Collaborative Selling.

Collaborative selling used to be a few sales reps chatting about an opportunity. Today, outside sales reps are calling the home office to speak with inside sales about the contact and their top three pain points. They’re also calling product managers and engineers, c-level executives, customer service, and even IT to discover potential customization offerings. It’s truly one of the most effective sales models today.

When prospects and clients learn of these collaborative efforts, they know it’s more than the outside sales rep standing behind them, it’s the whole organization. Talk about building customer loyalty!

16. Join Toastmasters or try an acting class

I have something to admit to you…

I used to be very shy. When the teacher would call me to the front of the class, I froze like a popsicle. Hard to imagine with my personal writing style, right?

After graduating and starting my first sales job, nothing seemed to change—until my sales mentor recommended that I attend the local Toastmasters. After only three months, my family and friends, and even my boss, couldn’t shut me up! I wasn’t just a huge extrovert all of a sudden. I was more confident in what I had to say.

If Toastmasters or other public speaking organizations aren’t for you, I would recommend a local acting theatre. Some of the best sales reps I know acted in high school or college, and some of them still do!

Now I’m not saying you should program yourself to act like a good speaker in front of prospects and customers, rather I’m saying you should find new ways to build confidence in your verbal and physical communication skills. It makes up over 75% of your sales career!

17. Take prospects and clients to dinner

Reciprocity is a powerful tool. You’re given a budget for meals and gas, but successful sales organizations know that there should always be an ample budget for taking prospects/clients out to breakfast, lunch, or dinner.

This is more than just doing “something nice” for someone. This is about changing the conversation’s environment.

Have you ever worked with a friend? When you chat with them by the coffee pot, your conversation is probably more professional and less casual. But when you change the environment to a bar during happy hour, the conversation radically changes to less professional and more casual chatter. However, if you keep the conversation focused on an opportunity, you’ll learn something new in both arenas.

This is one of the biggest reasons for taking leads and clients out, especially for dinner. The vibe from the social chatter, possibly one or two drinks, a hot nourishing meal, and the gratitude from a free meal can open your lead or client’s “vault” on the true budget, decision-maker, timeline, and many other key points that you can use to close the deal the next day.

18. Use Salesforce Caller ID

We’ve all been there. The phone rings. You look at the screen. It says, “1-123-456-7890, Boston, MA”.

You think to yourself, “Ugh! I have 100s of leads in the Boston area, who could it be?!”

Now imagine looking at your phone and the screen reads, “John Doe, $2.5 M opportunity, TJX Companies, 1-123-456-7890”.

How many more deals would you close if you knew that information before answering the phone?

Probably a lot! There are apps out there that can empower you with such immediate intel, such as Veloxy Sales AI. Of the 1,000s of happy users, this is always a fan favorite.

Next time you hit the road, don’t leave home without Salesforce Caller ID!

photo of veloxy's salesforce caller ID

19. Be yourself so your personality shows

Recall what I said about confidence and taking public speaking classes. It’s more about building confidence in your face-to-face communication skills, not about acting to close a deal.

Don’t let your seasoned communication skills and professionalism mask your unique personality. It’s usually your personality that attracts friends, partners, and long-lasting clients.

You could have a great sense of humor, or you may offer an empathetic ear to people, whatever it is, you should demonstrate it consistently. Just like marketers and outside sales reps focus on buyer personas, customers too will look for the personalities they like to work with and be around.

But be careful, your leads and customers may like you so much that they may try to friend you on social media, which brings me to my next and final outside sales secret.

20. Use social media (but be careful!)

Social media is a powerful tool in sales. While Facebook can be hit-and-miss based on your industry, Twitter and LinkedIn are great for demonstrating your thought leadership, brand authority, and overall willingness to help your prospects and clients.

LinkedIn is especially good for creating real connections with your target audience. Inside sales reps use LinkedIn Sales Navigator as a secondary email marketing platform. Here is an example of a cadence that outside sales reps like yourself could use:

Email Marketing: Email 1, Day 1 -> Email 2, Day 7 -> Email 3, Day 10 -> Call

Sales Navigator: Message 1, Day 3 -> Message 2, Day 5

Depending on the nature of your relationship with each connection, sales reps have even found it useful to tag connections in the comment section of LinkedIn and Twitter posts.

Lastly, when out in the field, make sure you have your leads and clients social media profiles accessible form your sales software. Visibility into their posts works great for creating new, relevant conversations.

21. Effective Time Management

Outside sales employees often have hectic schedules, requiring exceptional time management skills. To optimize their productivity, they should prioritize tasks based on their significance within the sales cycle. Structuring the day with a clear plan, including sales activities, prospect meetings, and follow-ups, helps maximize potential customer interactions.

Utilizing mobile sales technology and CRM tools allows sales reps to access critical information on the go, enabling seamless communication and data tracking. By strategically planning routes and appointments, sales reps can reduce travel time and focus on high-priority prospects.

Moreover, setting specific time blocks for administrative tasks, such as updating CRM records and drafting follow-up emails, ensures that sales employees maintain organized records and remain responsive to potential customers.

22. Build a Personal Brand

In the competitive world of outside sales, establishing a personal brand can set sales employees apart from their peers. Cultivating a professional online presence, including a well-designed website and active social media profiles, demonstrates expertise and builds trust with potential customers.

Sales reps should regularly share industry insights, case studies, and success stories to showcase their sales approach and problem-solving abilities. Engaging with relevant industry groups and participating in online discussions further establishes their thought leadership.

Presenting themselves as approachable and knowledgeable professionals creates a positive first impression, especially during face-to-face meetings with potential customers. A strong personal brand positions sales employees as valuable resources and reliable partners in addressing clients’ needs and concerns.

23. Active Listening

Effective communication is vital in outside sales, and active listening is an essential skill for sales employees to master. During interactions with potential customers, sales reps must pay close attention to their needs, pain points, and preferences.

By actively listening and asking insightful questions, sales employees can uncover critical information that informs their sales approach. Empathizing with potential customers’ challenges demonstrates a genuine interest in finding personalized solutions that meet their specific requirements.

Active listening also helps sales reps identify buying signals and objections, enabling them to tailor their sales pitch accordingly. Engaging in meaningful dialogue fosters stronger relationships with potential customers and increases the likelihood of converting leads into loyal clients.

24. Consistent Follow-Ups

A successful outside sales approach includes consistent follow-ups with potential customers. Sales employees should maintain regular communication with leads, providing updates, addressing queries, and demonstrating ongoing interest in their needs.

Utilizing CRM tools, sales reps can schedule follow-up reminders and track previous interactions, ensuring that no potential customer falls through the cracks. Personalized follow-ups, such as sending relevant content or addressing specific pain points discussed during previous conversations, show potential customers that they are valued and understood.

A structured follow-up strategy helps sales reps stay top-of-mind with potential customers throughout the sales cycle. Consistent and timely follow-ups reinforce trust, build credibility, and increase the likelihood of closing deals when potential customers are ready to make a purchase.

25. Networking and Relationship Building

Networking plays a significant role in outside sales. Sales employees should actively seek opportunities to connect with potential customers, industry peers, and decision-makers. Participating in industry events, conferences, and networking functions provides valuable face-to-face interactions with potential customers.

Outside sales reps can leverage these opportunities to introduce themselves, share expertise, and exchange contact information. Building genuine relationships fosters trust and credibility, laying the foundation for future sales interactions.

Additionally, outside sales reps should collaborate with inside sales teams and other colleagues within their organization. Sharing insights, best practices, and customer success stories can enhance the overall sales approach and provide a holistic view of potential customers’ needs.

Maintaining a robust professional network ensures that sales employees have a diverse pool of potential customers to engage with and increases their chances of generating quality leads and referrals. A strong network can lead to new opportunities, repeat business, and long-term success in outside sales.

26. Learning Between Inside & Outside Sales Teams

In the realm of sales, the phrase “knowledge is power” takes on new dimensions. One often-overlooked goldmine for ramping up sales effectiveness is the cross-functional training between your Inside Sales and Outside Sales Teams. Imagine the synergy when your Outside Sales Representatives grasp the intricate details of the CRM tools that Inside Sales use daily, or when Inside Sales understand the field challenges faced by Outside Sales.

  • Benefits:
    • Enhanced Sales Strategy
    • Improved collaboration and communication
    • Elevated conversion rates

This reciprocal learning not only deepens team cohesion but can be a game-changer in amplifying your Sales Strategy. Don’t underestimate the power of a well-rounded, cross-trained sales team!

27. Initiate Rotational Leadership Across Sales Teams

Ever thought about shaking things up a bit in your Sales Teams for a fresh burst of creativity and innovation? One way to do this is by launching a Rotational Leadership Program. In this transformative approach, your Outside Sales Representatives switch roles briefly with those in Inside Sales.

  • Key Advantages:
    • Exposure to varied Sales Strategies
    • Encounter different sets of challenges
    • Experience diverse customer touchpoints

This isn’t just job-swapping; it’s a multi-dimensional Sales Strategy aimed at continuous skill enhancement and team engagement. It’s about keeping the Sales Teams agile, knowledgeable, and ever-ready for the evolving sales landscape.

28. Conduct Bi-Annual Sales Strategy Reviews

In the ever-changing sales environment, a static Sales Strategy is a recipe for stagnation. To stay ahead of the curve, pencil in bi-annual strategy huddles that bring both your Inside Sales and Outside Sales Teams to the table.

  • Core Objectives:
    • Revisit and recalibrate existing tactics
    • Foster cross-pollination of best practices
    • Achieve strategic alignment between Inside and Outside Sales Teams

These aren’t just meetings; think of them as recalibration opportunities for your Sales Teams. A chance to sync up, share fresh insights, and tweak your Sales Strategy to adapt to market dynamics. Keep everyone on the same page and perpetually sharpening their saws.

29. Elevate Your Outside Sales Pitches with VR

In the crowded field of sales, standing out is non-negotiable. How about upping the ante by weaving Virtual Reality (VR) into your Outside Sales Strategy?

  • Key Benefits:
    • Amplified engagement during pitches
    • A multi-dimensional experience for potential clients
    • Competitive edge over both Inside Sales Teams and traditional Outside Sales Representatives

Don’t just tell, show—and let your prospects virtually step into the world of your product or service. Outside Sales Representatives armed with VR tech not only dazzle but also deepen the connection between the offering and the potential client. Say hello to a future-forward Sales Strategy that truly engages.

30. Harness the Power of Geo-Fencing

Welcome to the future of customer engagement: Geo-Fencing. This location-based technology is not just for digital marketers; it’s a game-changer for Outside Sales Teams as well.

  • Strategic Uses:
    • Triggering tailored promotions as potential customers enter predefined areas
    • Enabling real-time interactions that are tricky for Inside Sales Teams to emulate

Imagine a prospect walking into a competitor’s venue, only to receive a well-timed, persuasive promo from your Outside Sales Representative. It’s direct, it’s immediate, and it’s effective. This adds a dynamic, real-time layer to your Outside Sales Strategy, allowing you to be exactly where your customers are, virtually speaking.

Final Word on Outside Sales Professionals

With the new remote sales world we find ourselves in, outside sales can be forgotten about because of inside sales’ rise up the ranks. One thing is for sure, there are still industries and companies that demand outside sales representatives, and, outside sales reps deliver a more personal, face-to-face relationship, which most humans prefer over alternatives like video conferencing.

Here are some other outside sales resources for to help you grow your pipeline:

Share our Inside Sales Secrets with your SDR friends: 15 Inside Sales Tips That Actually Work

Read More:  Get the G2 AI Sales Assistant Software Momentum Report

Frequently Asked Questions

What is Outside Sales / Field Sales?

Outside sales is also referred to as field sales because of the location from which the sales rep works—anywhere in their territory. Also known as “road or air warriors” due to their high amount of travel, outside reps close their deals in person by visiting customers at their office, factory/plant, or anywhere the customer’s product is being used.

You can make the argument that the profession of outside sales was hit harder than any other job during Covid. These salespeople make their money by personally engaging with leads and customers face-to-face, and they rarely work from their company’s home office.

While working from home or a satellite office has advantages during Covid, outside sales reps have had to pivot and meet with leads and customers via video conferencing. This has been a challenge for most as outside reps are typically people-persons, extroverted, and they enjoy a hands-on approach, especially when demoing products.

For those contemplating a career in outside sales, you’ll flourish in your new role if you’re competitive, willing to travel two to three weeks a month, have deep knowledge of a product or industry (or aspire to), and you’re energized by the opportunity to make great commission checks.


Samir Majumdar

Samir Majumdar

Samir is the CEO and Co-founder of Veloxy. After spending 20+ years creating corporate systems, boosting revenue, and eliminating inefficiencies, Samir started Veloxy to help sales professionals shorten sales cycles, accelerate pipelines, and close more deals.

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