Enterprise Sales: 47 Experts Share their Top Tips for Winning at Complex Sales
It’s tempting isn’t it? The thought of closing a deal with an enterprise customer?
You earn substantial revenues, which might run into millions of dollars. You also add a well-known company to your customer list and this reputation makes it easier for you to close other deals.
However, selling to enterprises is extremely complex and far more difficult than winning deals with mid-sized companies or startups.
What Makes Enterprise Sales Tougher?
Here are just a few challenges of enterprise sales:
You don’t just sell to one or two people. An enterprise deal will have several decision makers. Additionally, there will be several people who you might never meet, but who will have considerable influence over the decision.
You will have to speak to a dozen or more people from different departments, attend several meetings and deliver multiple presentations.
And all this will take time. It usually takes at least 3 months to close an enterprise deal and might even take a year – sometimes longer!
How can you successfully navigate all these complexities of the enterprise sale, and win the business?
Asking the World’s Leading Authorities on Sales
To find out, we asked 47 of the world’s best-known sales experts about their advice on how to win at enterprise selling.
Who are these experts?
Most of them are consultants, trainers and coaches who Fortune 500 companies go to when they want to learn about sales.
Many of these experts have been recognized by Forbes, TopSalesWorld and Salesforce as the world’s leading authorities in sales.
Many are bestselling authors in the field of sales
Some of them are in executive roles in Training Industry’s Top Sales Training Companies of 2017.
Others are CEOs and senior leaders of companies who have had years and even decades of experience in selling to enterprises.
What these Experts told Us
Our experts gave us several tips for the multiple aspects of enterprise sales
1. How to accurately identify the prospect company’s needs, even if they don’t explicitly tell you.
2. How to identify companies that would be most likely to buy
3. How to identify the right decision makers within a company to approach
4. How to build relationships with the decision makers
5. How to position your offering for maximum impact
6. How to know who you are competing with for the deal
7. How to do better than your competitors
8. How to objectively assess if the deal is going in your favour or not
9. How to manage a sales team focused on enterprise prospects
10. And a lot more…
Here are our featured experts (in alphabetical order of last names)
47 Experts Share their Top Enterprise Sales Tips
(Note: All quotes given exclusively for the Knowlarity blog)
Steve Andersen is President and Founder of Performance Methods, Inc., a sales and account management best-practices consulting firm whose clients include industry leaders and many of the world’s top companies. He is the author of Beyond the Sales Process: 12 Proven Strategies for a Customer-Driven World (AMACOM/2016) and his expertise has been featured in a wide variety of sales performance media. Steve lives in Alpharetta, GA.
Bob Apollo is founder of Inflexion-Point Strategy Partners and creator of the Value Selling System®. He works with B2B companies who offer solutions that tend to be strategic purchases that have a lengthy and complex buying process involving multiple stakeholders.
Naomi Assaraf is co-founder and CMO of cloudHQ, a profitable tech startup that makes Gmail productivity tools for clients like Uber, Andreessen Horowitz, and HP. In the last 2 years at cloudHQ, she increased user acquisition by a factor of 7. Her main focus is growth, obsessing over the process of growing startups to their profitability stage.
She’s since done so for each of her 3 companies since her first one at age 17; which resulted in an exit. She mentors other startups on growth, is a global keynote speaker, and blogs for the Huffington Post. As an active member of the UploadVR collective, her most current interests revolve around artificial intelligence and mixed reality.
Irene Becker is a thought leader is business whose accomplishments include being first CEO of a steel company in Canada, developing one of the first business mentorship programs in the country and first woman Rotarian in Canada. Founded in 2003, Just Coach It provides Coaching, Career Coaching, Consulting, Training, Keynotes & Articles with a unique 3Q focus (IQ-EQ-SQ). She has earned several recognitions such as Top 100 Leadership Blogs, Top 50 Sales Management Blogs, Top 75 Human Champion-Switch & Shift, USA, Top 100 Employee Engagement Experts, Best 21st Century Leadership Blogs and more.
Butch Bellah is the owner of B2 Training & Development. He is a speaker, sales trainer and author of Sales Management For Dummies and The 10 Essential Habits of Sales Superstars. He’s been featured in Entrepreneur Magazine, Worth Magazine, The Boston Globe and all major networks. He lives just outside Nashville.
Steve Benson is the Founder and CEO of Badger Maps. After receiving his MBA from Stanford, Steve worked in Sales at IBM, HP and Google where he worked in the enterprise sales group. Steve was Google Enterprise’s Top Sales Executive in 2009. In 2012 Steve founded Badger Maps, the #1 Sales App in the Apple App Store, which helps Field Salespeople be more successful.
Kirsten Boileau is Head of Regional Engagement and Social Selling at SAP. She is responsible for the continued development of the stellar Social Selling programs at SAP. She is an evangelist for Social Selling, both internally and externally to SAP, speaking at events, writing blogs.
Jeb Brooks is President and CEO of The Brooks Group, a corporate sales training and sales management training company started by his father, Bill Brooks, in 1977. He is the author of four books, has visited 7 continents and has appeared in the Wall Street Journal, Money, Fortune, and CNN.
Bill Carmody is a contributing writer for Inc and the CEO of Trepoint, a digital marketing agency that solves problems and creates break through marketing that is as powerful as the clients they serve.
Jim Cathcart, Founder of Cathcart.com is the original author of Relationship Selling and Top 1% TEDx speaker. Inducted into the Sales & Marketing Hall of Fame by Top Sales World. He has written 18 books and delivered over 3,000 speeches worldwide.
Kevin F. Davis
Kevin F. Davis is president of TopLine Leadership, Inc., a leading sales and sales management training company serving clients from diverse sectors. Kevin has more than 30 years of experience in every aspect of sales, sales management, and sales training. He is the author of three books: “Slow Down, Sell Faster!”, “Getting Into Your Customer’s Head” and “The Sales Manager’s Guide to Greatness”.
Craig Elias has been recognized by Forbes as one of the Top 30 Influencers in Social Selling. He is he creator of Trigger Event Selling™ which resulted in him winning the $1,000,000 prize in Tim Draper’s Billion Dollar Idea Pitch Contest and gained him coverage on NBC, The New York Times, The Wall Street Journal and more. He is the author of award-winning sales book “SHiFT!” shows how to harness Trigger Events to win business.
John D. Elsey
John D. Elsey is President & CEO at Richardson, A Leading Sales Training and Performance Improvement Company. After a career in sales leadership, John has held a variety of CEO roles in the performance improvement industry since 2000. During this time, his work has focused on helping leaders grow revenues and enhance operating margins through excellence in leadership, strategy and sales execution in the Americas, EMEA and Asia.
Jon Ferrara has been recognized for pioneering innovation in the customer management category. Prior to founding Nimble, Ferrara was the creator and co-founder of the award winning customer management product GoldMine.
Peter is Founder and CEO of Momenta Systems Inc., Designers of Smart Funnel. His B2B sales and marketing began at IBM Data Processing division, and includes work with many smaller firms, an 18-year consulting practice, and over 80 published articles on revenue generation methods.
Patricia Fripp is a seasoned sales presentation skills trainer, executive speech coach and on-line training expert. Meetings and Convention magazine named Fripp “One of the ten most electrifying speakers in North America.” Her clients include Microsoft, ADP, Concur, First American, Visa, Blue Diamond Almonds and the American Payroll Association.
Joe Hart is President and CEO of Dale Carnegie Training, a worldwide leader in professional development, performance improvement, leadership training, and employee engagement.
A nationally recognized sales expert, Alice has made numerous guest appearances on television and radio broadcasts, in addition to being featured in print publications, including Entrepreneur’s Startups and Selling Power magazines. Alice developed her expertise in sales while at Miller Heiman, Inc. before striking out on her own. In her years at Miller Heiman she trained some of the company’s largest and most complex accounts including: Coca Cola, John Deere, Dow Chemical, Fidelity Investments and Hewlett Packard.
Leanne Hoagland Smith
Chief Results Officer,
Leanne Hoagland-Smith is a nationally recognized business building expert with over 3,000 published articles, a weekly business column, speaker and the Chief Results Officer for Advanced Systems, an international human capital talent development firm.
Jonathan M. Hodge
President and CEO,
Advantage Performance Group
Advantage Performance Group is a firm committed to providing a continuous stream of solutions and platforms that help leaders lead, sellers sell, and businesses to flourish. Advantage Performance Group has clients like Macy’s, Baxter, Sanofi Aventis, Holcim, Johnson Controls, Kroger, etc.
Mark Hunter, “The Sales Hunter” is a sales consultant who is equally well known for his high-energy, high impact sales kickoff programs. Clients include; Samsung, BP, Novartis to name just a few. He’s also the author of two best-selling books, High-Profit Prospecting and High-Profit Selling.
Keith Johnstone is the Marketing Manager of Peak Sales Recruiting, a leading B2B sales recruiting company launched in 2006. He has worked with a wide-range of clients including boutique, mid-size and world-class companies including P&G, Gartner, Deloitte, Merck, Taser and others.
Keith is an expert on B2B sales and recruiting matters, having his insights featured in HubSpot, Recruiter.com, HR.com, Docurated.com, etc.
Connie Kadansky, Managing Partner of Exceptional Sales Performance, LLC. provides the only assessment in the world that measures for the 16 types of Sales Call Reluctance. She also coaches salespeople to overcome Sales Call Reluctance™ (Sales Call Reluctance is a trademark of Behavioral Sciences Research Press). Her clients include AT&T, American Express, Nestle, New York Life, Best Western, etc. and her work has been featured in publications like The Wall Street Journal, Bloomberg BusinessWeek, Inc. and CEO Magazine.
Nick Kane is a Managing Partner at Janek Performance Group . He has trained more than 15,000 sales professionals worldwide during the course of his career, and is passionate about helping sales professional improve their selling careers – and as a result, their lives as well. Nick has co-authored a book called Critical Selling: How Top Performers Accelerate the Sales Process and Close More Deals which was released by Wiley Publishing in October, 2015.
Alice Kemper, Sales and Leadership Consultant, Coach and Speaker is founder of Sales Training Werks and Sales Training Consultants. Alice and her team stop your reps from driving you nuts and instead… drive 5 – 35% revenue bumps to crush their monthly quotas.
Craig is the founder and CEO of SalesNexus.com, a leading web based CRM, marketing automation and lead generation solution for sales teams from 10 to 100. Craig has written several popular books including “Inside-Out Selling, Forget Technique, Know Your Customer”, “Grow Sales with Emails – 7 Simple Steps Salespeople Can Take Today” and the recent “Email Marketing for Sales Teams – Best Practices”.
Sales Transformation Strategist,
Transforming Sales Results, LLC
Mike Kunkle is a renowned sales transformation strategist, practitioner, speaker, and writer. He’s spent 22 years as a corporate leader or consultant, helping companies drive dramatic revenue growth through best-in-class learning strategies and his proven-effective sales transformation methodology. Today, Mike is leading Transforming Sales Results, LLC, designing sales learning systems, speaking, leading webinars, and guiding clients through all aspects of their sales transformation.
Dave Kurlan, CEO of Objective Management Group and Kurlan & Associates is a Top Rated Keynote Speaker, Best-Selling Author and Sales Thought Leader.
Principal, Technology Finance Partners
Michael Nick is a bestselling author of several books on sales, sales process, and sales enablement. He has consulted with companies like HP, Rockwell Automation, Fiserv, Veritas, and Palo Alto Networks. Michael has trained thousands of sales professionals on value selling and financial acumen.
Erik Peterson is Chief Customer Officer at Corporate Visions. He is responsible for leading the company’s consulting team globally, including staff and certified contractors. Erik has delivered consulting engagements, keynotes, and messaging skills workshops to more than 10,000 marketing and sales executives in over 13 countries, and his team has done this work in 56 countries around the world.
Steve Richard is the Founder and CRO of Execvision. He’s a B2B sales and marketing expert and sales kickoff speaker, featured in The Washington Post, Bloomberg Business Week, Washington Business Journal, Harvard Business Review, CNBC, CNN/Money.
Linda Richardson is an award winning sales thought leader and the Founder of Richardson Sales Training. She is a Faculty at the Wharton Graduate School, University of Pennsylvania. Linda is the author of ten books on selling and sales management including: Perfect Selling, The Sales Success Handbook — 20 Lessons to Open and Close Sales Now, etc.
Steven A. Rosen
Steven Rosen, MBA, brings over 25 years’ experience, both on the ground and in the executive suite, to his work with individuals and organizations to transform sales executives and managers into true sales leaders.
He is author of 52 Sales Management Tips: The Sales Manager’s Success Guide, has been named Top Sales World’s Top 50 Sales & Marketing Influencers and publishes his award winning sales management blog.
Aaron Ross is a keynote speaker and bestselling author of ‘Predictable Revenue‘, called the “Sales Bible of Silicon Valley,” based on an outbound prospecting system that’s created more than $1 billion across Salesforce and other companies. He ‘s Co-Founder and CRO of Carb.io and Co-Founder of PredictableUniversity.com. His latest book, coauthored with Jason Lemkin is, ‘From Impossible to Inevitable‘.
Jill Rowley has been recognized by Forbes as one of the Top 30 Influencers in Social Selling. During her 20+ year career, she spent six years in consulting, 13 years as a top-performing rep in software sales at Salesforce and Eloqua, a year designing and deploying a global social selling program at Oracle, and is now evangelizing social selling internationally.
Neal Schaffer is a globally recognized leader in the world of business social media. In addition to be named one of marketing’s ten biggest thought leaders by CMO.com, Neal has also been recognized as a Forbes Top 50 Social Media Power Influencer as well as a Forbes Top 5 Social Sales Influencer.
Founder and CEO,
Hunt Big Sales
Tom Searcy is the Founder and CEO of Hunt Big Sales, a firm specializing in strategy, process development and training for transformational size account acquisition. Tom is also the author of 4 books on large account sales including the best seller, “How to Close a Deal Like Warren Buffett” with Henry Devries. Using his system companies have landed over $10 billion dollars in new sales.
Kurt Shaver specializes in teaching sales teams how to leverage social networks like LinkedIn to grow sales. In the past six years, more than 20,000 people have improved their social selling skills via his corporate training and speaking appearances at conferences like LinkedIn Connect and Dreamforce.
Amar Sheth is VP of Customer Success at Sales For Life and has trained thousands of people worldwide on the topic of Social Selling.
Sales For Life is a global authority in Social & Digital Selling Education, helping B2B organizations achieve behavioral changes to drive pipeline and revenue across the board.
Colleen Stanley is an author, speaker and trainer on Emotional Intelligence For Sales Success. Salesforce has named her as one of the most influential sales figures in the 21st century.
Brian Sullivan is the Vice President of Sandler Enterprise Selling at Sandler Training. Prior to joining Sandler in 2012, Brian was in sales, sales management and P&L management positions with The Cap Gemini Group for thirty years and in sales positions with Xerox Corporation prior to his time with Cap Gemini. Brian is the co-author of Sandler Enterprise Selling: Winning and Growing Enterprise Accounts and he is a frequent contributor to blogs and articles in business publications.
Babette Ten Haken
Babette Ten Haken is a corporate strategist and facilitator. She writes, speaks, consults and coaches about how cross-functional team collaboration revolutionizes the industrial Internet of Things (IIoT) value chain for customer loyalty, customer success and customer retention. Her One Millimeter Mindset™ programs draw from her background as a scientist, sales professional, enterprise-level facilitator, Six Sigma Green Belt and certified DFSS Voice of the Customer practitioner.
Author of ‘GoforNo’
Andrea Waltz is a professional speaker and co-author of Go for No! She teaches audiences how to overcome fear of failure and rejection to achieve their personal and professional goals and dreams.
Craig Wortman is Founder and CEO of Sales Engine Inc. and Founder & Executive Director of the Kellogg Sales Institute at Kellogg School of Management. He is a renowned speaker on subjects of leadership, high performance selling, entrepreneurship, and the power of story. He is the author of book on leadership called “What’s Your Story?” At Kellogg, Craig teaches a course called “Entrepreneurial Selling” which was ranked as one of the Top Ten courses in the country by Inc. Magazine.
Rene Zamora is the founder of Sales Manager Now and author of Part Time Sales Management which will be published later this year. Rene is a pioneer in contract or outsourced sales management, starting his company in 2006. He has perfected the ability to manage many sales teams simultaneously in a Part Time fashion, which he shares in his book. His approach has reduced sales management cost and increased revenue per sales rep with his clients.
Enterprise sales might be complex, but if you follow these tips, you will find it far easier to crack win these high-ticket deals.
Which of these tips would you start to apply? Are there any other useful tips that you would like to share? Tell us in the comments section below.