The Complete Guide to Enterprise Sales (2022)

What are the challenges of enterprise sales?

The world of enterprise sales is not without its ups and downs.

The sales cycles are longer.

It can take months or even over a year to close a deal. That’s a lot of time to keep working and to keep the faith. It also leaves a lot of time for things to go wrong, or fall part entirely.

The room is bigger — and reading the room is harder.

We have to be smart about understanding the complexities of organizational behavior, and understanding the key influencers. If we don’t, we can waste a year trying to sell to the wrong people.

The selling motion needs to be airtight.

When we do find the right people, we need to be prepared to speak their language and solve their problems, or they’ll move on to the next thousand people who are trying to sell them something. That’s why we can’t do this alone. It takes a team with all kinds of expertise, working in lockstep, to close an enterprise deal.

The Complete Guide to Enterprise Sales (1)

How do I create an enterprise sales model?

So you’re ready to take the plunge into enterprise sales? Follow these steps.

Sell the right thing.

Did you remember to build an enterprise-friendly product? There will always be companies with promising products for commercial accounts that go after the enterprise — and fail. Sometimes it comes down to not solving a problem that enterprise customers care about. More often, it comes down to scale. Can the product work for thousands of users? Can it scale to millions of cases a day?

Focus on the sweet spot in your market.

Enterprise sales comes with tough decisions about which accounts you decide to go after — and which accounts you don’t. How can you get more prescriptive, more dedicated, and more intentional? How can you get more proactive?

If you’re an account executive initially going after the enterprise market, and you’ve landed a Fortune 50 company, you simply can’t go manage a hundred other accounts. The enterprise go-to-market model carries a temptation of spreading yourself too thin. To avoid this temptation, put yourself where the highest chances of success are, and forget about everywhere else.

Get into “solutioning.” (And here’s what that actually means.)

In commercial sales, where we’re selling to small and medium businesses, we’re taking our demos and giving them a quick rinse and repeat. But in enterprise sales, we need to do more than swap out logos on a deck. We need to really step into the customer’s shoes and show them that we’re knowledgeable about their business challenges, their competitive space, and their strategy for growth.

Then, as we engage with executives to validate our ideas for how to solve their problems, we earn the right to come back and present those ideas over time. That’s solutioning — and it’s why enterprise sales reps are more like consultants or trusted advisors.

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How do I build an enterprise sales team?

How will we prove business value to the chief financial officer? How will we prove ease of implementation and back-office integration to technical leadership? How will we get board approval?

Enterprise customers need a thorough selling motion that brings in different skill sets, from digital advisors to solution architects. Completing the enterprise sales process takes diverse and brilliant thinking all the time — and at scale. Visit Trailhead to learn about the best hiring practices for sales teams.

Enterprise sales team structure

Sales Leader

(Video) The 17-Minute Guide to Enterprise Software Sales

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Directs a sales team and brings together sales channels to plan for growth — and make it happen

Account Executive

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Manages existing customer relationships and finds opportunities to build new ones

Digital Advisor

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Creates a digital transformation plan that applies the latest technologies to the deal

Solution Architect

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Shows how a solution can be implemented in a customer’s IT environment

Customer Success

(Video) The 17-minute Guide to Enterprise Software Sales — The Startup Tapes #029

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Improves the customer experience and increases adoption and use of the product

Business Development Representative

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Generates new, qualified prospects through cold outreach

Give your team the sales training they need for career-long success

Discover skill-up courses on the Salesforce learning platform, Trailhead, designed for everyone in the sales community — from business development representatives (BDRs) to aspiring chief revenue officers (CROs). These learning paths (aka "trailmixes") cover critical sales skills, like prospecting and cold calling; soft skills; sales tool tips; and leadership best practices. Plus, it’s all free!

Browse the trails

The art and science of enterprise sales

Enterprise sales is an art. We paint a vision of the future, and we bring along a transformation roadmap to get there. It’s also a science. We keep the lights on, we run the end-to-end business, and we keep an eye on metrics. Read how dashboards can help you track all the numbers that matter.

Enterprise sales metrics that can measure your team’s success

Run rate

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A prediction of upcoming revenue for a longer period of time (usually one year), using current financial data

Win rate

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The percentage of opportunities (potential customers) that are closed to become actual customers

Customer retention

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The percentage of customers who continue to buy and renew over time, creating recurring revenue


Customer lifetime value

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A prediction of how much money a customer is expected to spend on your company over their lifetime

(Video) The Complete Guide To Software Sales Career Path

Pipeline velocity

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How quickly deals move through your pipeline (the stages of your sales funnel) and generate revenue

Pipe coverage

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A ratio that compares the sum of all your sales opportunities with your quota (revenue target)

Hiring an enterprise sales team

We need to hire people who can carry both the art and the science inside their heads at all times. That’s not easy. This principle can help: Hire for character, train for skill.

Here are the traits to look for:

Long-term and short-term balance

Patience and urgency may seem at odds with each other. Not in enterprise sales. If we play the short-term game with a customer and sacrifice long-term value for immediate gains, then we can stumble and never recover because in business — as in life — everyone talks. We have to be willing to play the long game while collecting little wins along the way.

Curiosity and creativity

Enterprise sales is complicated. (We’re not exactly selling shoes.) So we have to constantly learn, go and understand a problem, and build a solution message around it — a story. At the beginning of an enterprise sales deal, we face a big, blank space, and it’s up to us to fill it in. Curiosity and creativity will get us there.


At Salesforce, maybe it seems like it’s easy for us, but we work hard for every dollar. Enterprise sales reps are thinkers and strategists, but we’re also scrappy and eager to put in the work, and that will never change.


What we do takes leadership to bring together the full force of selling, support, and acting as partners to the customer and their journey.

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How can I succeed in enterprise sales?

So now you’ve built your team of rockstars, you’re showing enterprises their future, and you’re mapping that vision back to what you want to sell. You’ve got products installed on the customer base, and you’re feeling good.

Think again — because you haven’t reached the mountain top. You’ve reached a plateau. The question is this: How are you going to take things to the next level, where you’re adding products, building customer relationships for life, and growing your business?

Forget about all the things you hear about great leadership, integrity, and values. Yes, fine, but those are table stakes. At the end of the day, the best enterprise sales reps are focused on these three things.


How do I get good at enterprise sales? ›

We've compiled a list of ways to help you succeed in enterprise sales.
  1. 1) Define your objectives.
  2. 2) Analyze customer's business process to address pain points.
  3. 3) Know the different stakeholders and understand their role in the sales process.
  4. 4) Always have an agenda and send it out in advance.

What is enterprise sales process? ›

Enterprise Sales or Complex Sales refers to the process of selling to large b2b companies. The selling cycle is like no other, risks are much higher, and several departments are involved from start to finish. It is worth noting that the selling process does not end after the sale is made.

What skills do you need for enterprise sales? ›

Enterprise software sales professionals must possess presentation skills in addition to being adept at relationship-building, negotiation, and communication. Since enterprise sales tend to be for an entire company, they tend to be high-dollar-value sales, involving multiple decision-makers.

What makes an enterprise sales succeed? ›

Because enterprise sales produce high-value deals and a longer sales cycle, it's essential to build brand credibility before moving beyond transactional sales. Having the sales team relationship building with prospective clients is a sure way for enterprise sales to succeed.

How difficult is enterprise sales? ›

It should be a shock to no one – the larger the sale, the more complex the sales process. Of all the types of sales, enterprise sales is the most lengthy and complicated. It requires more touchpoints, better strategies, and a longer-term plan than traditional SMB sales.

Is enterprise a stressful job? ›

It's a very competitive environment to work in. Your sales statistics are posted each month, and you are ranked in your office. It can be a stressful and demanding job.

What are the 7 selling process? ›

There are seven common steps to the selling process: prospecting, preparation, approach, presentation, handling objections, closing and follow-up. The first three steps of the selling process involve research into prospects' wants and needs, with your presentation midway through the selling process.

What are the 3 enterprise skills? ›

Enterprise skills encompass a number of things including:

Innovative and original thinking. Problem solving. Prioritisation. Strategic thinking.

What are the 8 enterprise skills? ›

communication; • team work; • problem solving; • initiative and enterprise; • planning and organising; • self-management; • learning skills; and • technology.

What are the 3 most important selling skills? ›

Top 5 skills for a career in sales
  • Confidence - maintaining a positive attitude.
  • Resilience - communicating with conviction.
  • Active listening - understanding the customers' needs.
  • Rapport building - selling your personality.
  • Entrepreneurial spirit - continual self-improvement.

How much do top enterprise sales reps make? ›


How do you speed up the enterprise sales cycle? ›

How to Speed up the Enterprise Sales Cycle
  1. Adjust Your Internal Approach. ...
  2. Take a Multi-Threaded Sales Approach. ...
  3. Bring the Right People Into Your Demos Early On. ...
  4. Personalize Conversations and Content. ...
  5. Nudge Enterprise Prospects Along with a Gift. ...
  6. Bring in Your CEO.

What is the toughest part in sales? ›

But hands down, prospecting has been chosen as creating the most difficulty for reps. In fact, “more than 40% of salespeople say this is the most challenging part of the sales process, followed by closing (35%) and qualifying (22%),” HubSpot explains.

What is the hardest form of sales? ›

The hardest part of sales is not rejection or being said no to over and over again. After a short time making sales, you get past those fears and just see them as part of the job. The hardest thing and the thing most salespeople fail to do properly is consistently and effectively following up.

How long is enterprise sales cycle? ›

Enterprise sales cycles are typically 7+ months and 6+ figure deals. It takes a concerted effort between the sales rep and the prospect to move the deal forward through multiple stakeholders and multiple stages. The emphasis on process becomes more important as the odds of closing the deal diminish.

What is the number 1 most stressful job? ›

Based on these factors, the ten most high-stress jobs in the world, according to research from the US News Best Jobs database, are:
  • Mental health counsellor. ...
  • Anesthesiologist. ...
  • Patrol officer. ...
  • IT manager. ...
  • Construction manager. ...
  • Physician. ...
  • Lawyer. ...
  • Financial manager.
17 Jun 2022

What is the hardest job to hire for? ›

What are some of the hardest roles to fill? The hardest roles to fill are tech workers, healthcare professionals, sales, and product/project managers based on recorded data. Let's find out why recruiters and talent acquisition professionals have difficulty finding talent in these fields.

Can you make a lot of money at enterprise? ›

Salaries at Enterprise Rent-A-Car Co range from an average of $32,415 to $77,520 a year. Enterprise Rent-A-Car Co employees with the job title Manager Trainee make the most with an average annual salary of $44,000, while employees with the title Manager Trainee make the least with an average annual salary of $44,000.

What are the golden rules of sales? ›

6 Golden Rules For Success in Sales
  • 1 - Call As High As You Can. ...
  • 3 - Sell Aspiration. ...
  • 4 - Recruit a Coach. ...
  • 5 - Always Be Prepared to Walk Away. ...
  • 6 - Talk About Money Early, and Price Late.
15 Aug 2011

What are the 5 sales techniques? ›

Here are five selling techniques every salesperson should master.
  • Active Listening. One of the reasons that prospective clients are so wary of salespeople is because they anticipate a pushy demeanor and pressure to purchase a client. ...
  • Warm Calls. ...
  • Features & Benefits. ...
  • Needs & Solutions. ...
  • Social Selling.
11 Nov 2016

What are the 4 selling strategies? ›

The four basic sales strategies salespeople use are script-based selling, needs-satisfaction selling, consultative selling, and strategic-partner selling. Different strategies can be used with in different types of relationships.

What are the 6 ps for purposeful selling? ›

The building blocks of an effective marketing strategy include the 6 P's of marketing: product, price, place, promotion, people, and presentation.

What are the 10 steps to a sale? ›

10 Steps To Sales Success
  1. Prospecting Stage. ...
  2. Qualifying Stage. ...
  3. Initial Meeting & Needs Discovery Stage. ...
  4. Needs Analysis. ...
  5. Presentation/Product or Service Demo. ...
  6. Proposal/Quotation Presentation. ...
  7. Influencer Approves. ...
  8. Key Decision Maker Or Committee Approves.
15 Dec 2014

What are the 4 A's in sales? ›

The "four A's" of sales letters are attention, appeal, application, and action.

What are 3 selling techniques? ›

  • Product Selling. Product selling is exactly what it sounds like: selling the advantages or features of a specific product or service. ...
  • Solution Selling. Solution selling goes beyond simply selling products or services. ...
  • Insight Selling.
1 Mar 2017

What are the 6 steps of sales? ›

The six steps are the pre-approach, the approach, the presentation, the objection, the close, and the follow-up. Before a salesperson shows a customer a product, he or she must carefully prepare for the interaction with the customer.

What are the four core areas of enterprise? ›

The Four Types of Enterprise Systems
  • Enterprise Resource Planning (E.R.P.) Systems. ...
  • Supply Chain Management (S.C.M.) Systems. ...
  • Customer Relationship Management (C.R.M.) Systems. ...
  • Knowledge Management Systems (K.M.S.)
25 May 2021

How can I improve my enterprise skills? ›

7 ways to proactively develop your entrepreneurial skills
  1. Refine your interpersonal skills. Be confident, friendly and approachable–consistently. ...
  2. Connect with other entrepreneurs. ...
  3. Join communities in your industry. ...
  4. Make a book list. ...
  5. Practice resilience. ...
  6. Ringfence time to de-stress. ...
  7. Keep your learning active.

What are the 5 skill levels? ›

The scale ranges from proficiency levels 1-5:
  • NA - Not Applicable.
  • 1 - Fundamental Awareness (basic knowledge)
  • 2 - Novice (limited experience)
  • 3 - Intermediate (practical application)
  • 4 - Advanced (applied theory)
  • 5 - Expert (recognized authority)

What are top 5 skills employers look for? ›

The top 5 skills employers look for include:
  • Critical thinking and problem solving.
  • Teamwork and collaboration.
  • Professionalism and strong work ethic.
  • Oral and written communications skills.
  • Leadership.

What are the top five valued skills? ›

The soft skills that may be most important in a changing job market for 2022 and beyond, according to McKinsey, include:
  • Critical thinking skills.
  • Communication skills.
  • Mental flexibility.
  • Teamwork ability.
  • Self-leadership.
  • Digital fluency7.

What are 5 good qualities of sales person? ›

5 Qualities That Make a Great Sales Person
  • Communication Skills. Sales is basically all-day communication. ...
  • Drive. A great salesperson needs to be passionate about what they do and have a drive to be successful. ...
  • Patience. Similar to commitment, a good sales person must also have a great deal of patience. ...
  • Empathy.
24 Sept 2018

What are the 5 C's that are important to be a great sales person? ›

In today's market environment, effective selling involves building trust through the use of five C's: conversation, curiosity, collaboration, customization and coaching.

What are the top 3 things a salesperson should not possess? ›

You're unable to ask the right questions. You have a sense of entitlement for being so good at what you do. Everyone is a prospect. You lack genuine social empathy.

What are three core skills of a salesperson? ›

Prospect-focused sales rep skills
  • Persuasiveness. Good salespeople don't pressure prospects—they persuade them. ...
  • Empathy. Walk a mile in each of your buyer's shoes to understand their needs. ...
  • Active listening. A critical part of selling is listening more than you speak. ...
  • Relationship building.
28 Sept 2021

What makes a poor salesperson? ›

A bad salesman is someone who is not good at selling products or services. They may be unprofessional, have a bad attitude, or be pushy. If you're looking for a good salesman, avoid these four types of bad salesmen. By doing so, you'll save yourself a lot of headaches and frustration!

What type of salesmen make the most money? ›

They're listed here from highest to lowest total average compensation.
  1. Enterprise Sales/Account Executive. Average salary: $75,000. ...
  2. Pharmaceutical Sales Representative. Average salary: $81,798. ...
  3. Realtor. ...
  4. Medical Device Sales Representative. ...
  5. Sales Engineer. ...
  6. Software Sales Representative. ...
  7. Major Gifts Officer.
26 Jan 2022

What type of sales rep makes the most money? ›

What do the highest paid sales reps sell in 2022? It's clear that the highest paid salespeople all work in the technology industry. Technology salespeople are getting paid about 20% more on average in 2022 compared to 2021.

What is the highest position in sales? ›

Chief sales officer (CSO)

A chief sales officer (CSO) is the highest sales position in an organization. A CSO is the person in charge of leading and managing the entire sales function of a company. They manage the company's VP of sales and oversee all sales activities of the company.

How do you increase sales 10 times? ›

What Is The 10X Rule? Put very simply, the 10X rule is taking any goal you've set for your company or sales team, and multiplying it by 10. So if a goal is to increase revenue by 5%, using the 10X rule, you'd increase that goal to 50%.

How can I increase sales in 3 months? ›

You can do this by making sure you're reaching them with the right marketing strategy. Search Engine Optimization (SEO) is found to be a necessity for businesses to get over walls and difficulties in growth.
6. Optimize Voice Search
  1. Use long-tail keywords.
  2. Use organized and structured data.
  3. Increase local presence.

What are the 3 stages of sales? ›

Three Stages to Sales Process
  • 1 – Qualification.
  • 2 – Collaboration.
  • 3 – Negotiation.
29 Jun 2012

How can I drive faster in sales? ›

  1. Be Present With Clients And Prospects. ...
  2. Look At Product-To-Market Fit. ...
  3. Have A Unique Value Proposition. ...
  4. Have Consistent Marketing Strategies. ...
  5. Increase Cart Value And Purchase Frequency. ...
  6. Focus On Existing Customers. ...
  7. Focus On Why Customers Buy. ...
  8. Upsell An Additional Service.
30 Mar 2021

How much do enterprise software sales make? ›

How much does an Enterprise Software Sales make in the United States? The average Enterprise Software Sales salary in the United States is $98,718 as of October 27, 2022, but the salary range typically falls between $89,728 and $107,774.

Does Enterprise give commission? ›

How much can I earn and how are commissions paid? Partners can earn a commission up to 2.5% on all qualifying revenue generated when a customer links directly from your site to the specific participating Enterprise branded site and makes a reservation resulting in a rental.

Do Enterprise agents make commission? ›

Agents register for one of four commission rates that range from 5% on highly discounted car rental rates to 15% for the standard rental rates. To date, more than 3,000 agents have signed up for the program. For more information, log on to, or call (800) 424-1282.

Why does Enterprise charge $200? ›

The company holds this sum to guard against scenarios like an accident, late return or additional fuel charge. Always ask how much will be held on your card and when you can expect your deposit back. It usually depends on the type of car your rent, where you pick up the car, and how you pay.

What type of salesperson makes the most money? ›

11 highest paid sales jobs
  • Pharmaceutical sales representative. ...
  • Direct sales representative. ...
  • Business development representative. ...
  • Sales engineer. ...
  • Sales professional. ...
  • Sales manager. ...
  • Real estate agent. National average salary: $107,989 per year. ...
  • Vice president of sales. National average salary: $110,945 per year.

What are 4 general way to increase sales? ›

increasing your prices. finding new customers. selling more to existing customers. offering sale promotions to boost the volume of sales.

What are 4 ways to attract customers? ›

Every small business owner wants to attract new customers. Here are 10 time-tested ways to help you bring in “new blood.”
  • Ask for referrals. ...
  • Network. ...
  • Offer discounts and incentives for new customers only. ...
  • Re-contact old customers. ...
  • Improve your website. ...
  • Partner with complementary businesses. ...
  • Promote your expertise.
6 Apr 2017

What is a good commission rate for sales? ›

However, the typical commission rate for sales starts at about 5%, which usually applies to sales teams that have a generous base pay. The average in sales, though, is usually between 20-30%. What is a good commission rate for sales? Some companies offer as much as 40-50% commission.

Can you make a million dollars in software sales? ›

The math is simple. A sales rep who attains 300% of their $2m quota will deliver at least $3m in extra profit for their firm. There is plenty of room for commission pay-outs in this model. Making $1m in software sales is an extremely rare feat.

Is software sales a stressful job? ›

The reality of any sales position is that you'll encounter stress. It's simply the nature of the job. Whether you're trying to meet a monthly quota, close a particularly large sale, or have a difficult manager who is always riding you, stress is part and parcel with sales.


1. Startup Sales vs. Enterprise Sales | SaaS Sales Comparison
(Patrick Dang)
2. Enterprise Sales 101 for Tech Startups
(SP Home Run Inc.)
3. How To Evaluate a Great Enterprise SaaS Sales Person
(Dan Martell)
4. How to Close Enterprise Sales: Learn How to Effectively Navigate Group Buying
(TK Kader)
5. Secrets To Combining PLG and Enterprise Sales with @Grammarly CEO Brad Hoover
6. Modern Realities of the Complex Enterprise Sale - Open Workshop, Nov 2022
(Winning by Design)

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