Yup, you read it right. One hundred and eleven sales enablement tips from experts in the industry.
From how to organize your sales content and deliver kickoff sessions to understanding customers’ jobs-to-be-done and saying ‘no’, this list has got it all - and more.
So, buckle in, bookmark this page, and don’t stop till you get to the end!
1. Don’t talk at the reps. Make it all about them and their success.
2. Involve the salespeople as much as possible and align tools and assets to the organization’s sales process (incl. categorizing tools into stages).
3. Have a formal process in place for your sales team to add content requests, which makes it easier for you to track and adjust dates amidst competing priorities. This also avoids several people working on the same request due to ad-hoc, 1:1 conversations.
4. If your sales team is small, have open conversations with them and make sure they can make requests and give feedback.
5. Find a way for weekly check-ins with the sales team. There is no substitute for relationship building with the sales team and hearing their needs.
6. Understand your customer jobs-to-be-done and where you can uniquely deliver value.
7. Consult with sales to determine priorities and develop your sales enablement roadmap. Don't guess what they need or else you'll spend cycles on tools and training that they don't actually need.
8. Research. Listen to the CUSTOMER, not just the sales team. Be prepared to do some presales to get air time for the research.
9. Treat your salespeople like an internal customer.
10. Don't be a "yes person." You'll lose track of higher priority items that can make more of an impact. It doesn't mean you should say no all the time, it just means you should be thoughtful and strategic. If you get a random request dropped on your desk and you're not yet sure how to proceed, don't just say "yes, I’ll do it." Come back to it later when you've thought more strategically and provided your best recommendation.
11. Treat sales enablement assets as if it's a legally binding document, and study it thoroughly.
12. Be consistent with your efforts and produce at scale.
13. Set a regular rhythm, focus on the top 3-5 things that will help the team move the needle, and hold reps accountable for consuming content and using content/messaging/tools.
14. Say no occasionally.
15. Over-communicate during periods of transition, whether in process or deliverables.
16. Communicate with sales to understand their needs and how they use what is produced.
17. Communicate as early and often as possible to stay on top of the sales teams’ needs.
18. Quarterly training - and starting those training sessions with a clear/compelling explanation of what you do and how it fits in.
19. Listen in to calls. Show you care while learning about the customer.
20. Conduct a retrospective on every sales campaign; really dissecting what worked and what didn't shows where enablement is needed or what needs to be broadly socialized because it's effective.
21. Find allies early and often. Make sure that you are showing them WHY what you are doing matters. Find ways to use them to get to the data that you need, not anecdotal evidence.
22. Your salespeople are also like your customers. Treat them well and they will treat their customers well. Build content and strategy in accordance with their strengths.
23. Be aligned with sales leadership on what you need to accomplish.
24. When creating sales materials think like a salesperson. What will help them increase sales and earn better commissions? What is critical for them to know about the customer's profile that helps them to better sell?
25. Think of sales enablement as a holistic framework.
26. No sales rep is the same, so keep your materials and insights relatively simple for the team, but have side options available for those ambitious reps who want to dig deeper on their own time.
27. Listen to what your reps are asking for, it's not always another datasheet.
28. Keep it short and simple.
29. Ask value prompter questions before talking about you or your product.
30. Listen to the buyers/prospects and create enablement for them, not the reps.
31. Don't get swept up into feature/function comparison.
32. Make sure the leaders put pressure top-down, with stats and engagement numbers to back it up.
33. Build a culture of delivering value.
34. At some point, launch success will shift from primarily a creative marketing push, to ensuring your reps and partners are prepared to sell on day one. To do that effectively without adding a ton of extra time to your launch sequence, get ready to get good at prioritizing content, and company-wide communication of a clear plan.
35. Get your sales leaders to prioritize their asks and agree to a timeline to deliver them. Avoid the never-ending mountain of requests - have a process.
36. Teach them how to use the enablement tool, don't just give it to them.
37. Manage expectations and upskill sales reps.
38. Empathy. You need to always step into the mind of your sales team, and your customers. It's like method acting, but for marketers.
39. Build the relationship bridge before you build the content.
40. Listen to salespeople! They are on the frontlines with customers every single day. Find a handful whose insights you trust and connect with them regularly.
41. Be willing to 'join' the team (e.g. to do a sales call, to role play, to pitch, etc.)... don't be hands-off/ivory tower.
42. Whenever you start creating any new tool, get buy-in from sales leaders first, so when it's ready it gets the appropriate visibility directly by being actively promoted by them, and is ultimately used as originally intended.
43. Come together and figure out enablement with sales enablement if there is that function. There tends to be friction between marketing and sales, but if you leave your ivory tower and work hand in hand then things will come together. Then get your top sales reps to be advocates for your efforts.
44. Your templates are a guide, not a mandate.
45. Regular sales enablement sessions. We do weekly Whiteboard Wednesdays, and it's invaluable to get the team together every week even when there's not a heavy enablement agenda.
46. Simplify the product's story.
47. Do not rely on content only to enable your teams. The 10/20/70 rule of learning is true for enablement.
48. Try to keep open communication around what is working for your sales team and what they think wins them the deals.
49. Make the sales team part of developing enablement material as its key for successful engagement.
50. Set-up a cadence to hold you accountable to discuss & review sales enablement with sales leadership - transparency will go far in building trust and a strong partnership.
51. Start small and then scale it.
52. Keep it simple and easy to understand and communicate.
53. Never stop being curious.
54. Talk to sales and customers, and iterate often.
55. Get buy-in from a couple of the highest performing and most valued sellers in the company. Let them have a first view on what's being generated and get their thoughts on how the message would resonate most with their peers.
56. Create role-based training and content, rather than lumping all sales roles together.
57. Start with the customer - what do you want them to take away from this launch or update then work backward.
58. Listen to the need and root of the issue and design a solution based on that.
59. Without a coaching cadence, nothing will be remembered.
60. Focus on the things you can influence. And play the long game.
61. Make it fun and easy to understand, repeat, train, repeat, reinforce --- it’s a continuous loop.
62. Understand how hard selling can be and be seen as someone who is there to make things easier.
63. Know what the customer values and how they want to be engaged and your sales team will move in that direction.
64. Make it a story - involve people - make it a discussion.
65. Salespeople are efficient - make it easy to sell.
66. Make sure you stay grounded and don't just live in enablement theory. If what you create isn't adopted or understood it's not going to be effective.
67. Create a single source of truth for sales. It's important that they feel that there's a singular place to go to for everything they need.
68. Sales relationships are a two-way street. They look to you as a product expert and can teach you a lot about your customer.
69. Think about your audience and constantly answer the "so what" in every enablement session. Why should they care and how will this content help them be better, faster, stronger in their role?
70. Don't ever think of sales enablement in a silo.
71. Get your sales leadership team onboard or you’ll find it hard to get your sales team to care.
72. Modularize sales enablement collateral for scalable personalization on the reps' part. For instance, create building blocks for product demo screenshots for different products, verticalized messaging blocks, header/footer design components, proposal deck slides for different business models and comparison charts, etc.
73. What will scale? One loud person doesn't speak for the entire sales or customer base.
74. Sales enablement can't be something you do just at the release of a new product or version. You have to constantly be in front of your sales teams helping them increase your knowledge and changing tactics based on the market or competition.
75. Be present and become the go-to resource for the team. Make sure it's clear what you're there for. Ask and act on feedback. Answer questions quickly or set up an SLA for response delivery for the team.
76. Get buy-in from the leadership of sales, product, and marketing to present as a unified front to the sales team.
77. To inform your efforts – keep asking questions until you get to the foundational "why it matters" or "how it will help clients."
78. Create a sales enablement structure that helps sales to be accountable for owning the product. Certifications, gamification, and measurable metrics around collateral use and modification are essential.
79. Always repeat and reinforce information, with the product's value or benefit to ICPs front and center.
80. Be engaged day-to-day.
81. Salespeople want to be enabled by salespeople that win. Have reps with early successes present their approach back to their peers. Structure their session for them, with the message you both agree is most powerful.
82. Engaging presentations! Video, video, video!
83. Sales enablement is a two-way street. It is as much a part of sales as much as it is a part of marketing. So ensure that you always have a channel for free-flowing conversations between the two teams.
84. Be the bridge to all other teams by providing insights that can help every other team. Communication should be a two-way street between sales/marketing, sales/product, sales/customer success.
85. Join standing meetings across your stakeholder/internal customers to understand themes and get a pulse of what's really happening in the field.
86. Earn your cred. If you’re in tech KNOW your tech. Develop a few key assets that you can prove out by knowing your tech.
87. Know how and when sales reps connect with the customer, and accordingly build dynamic content for them. Static slides or one-pagers are not going to be useful as the narrative changes for every person, region, stage of cycle. Rather, build a DIY kit to guide reps on which slides to use and when is a better way to make sure content is utilized.
88. Look at the questions prospects ask and ideate on how to empower them to get buy-in from their bosses.
89. Accessibility - if your materials and messages aren't accessible, efficiently organized, and shared in a timely manner, they won't make a difference.
90. Get as much first-hand reporting of customer reaction to the materials as you can. "Ridealongs" are best, post-call feedback is next.
91. Sales > demand generation. There is nothing more valuable than providing a sales rep with timely help/content to close or move an opportunity forward. Define what they need, where it fits into other priorities, track and share success with the broader team. If you're juggling responsibilities, make sure you're giving the sales teams some love. It'll foster a better sales-marketing relationship, which is key to revenue-generating success.
92. Show the sales rep that what you’re telling them will help them to make more money.
94. Deliver the message in different ways to account for how your team members learn and process new information.
95. Get close with the sales team. Attend meetings, be present on Slack or other communication channels, and be an advocate for their requests.
96. Map out the close process - then shorten it by reducing barriers.
97. Don't just leave it to the docs, present.
98. Be concise, be repetitive.
99. You can’t please everyone.
100. Make sales accountable by tracking who has taken training.
101. Focus on what will make the largest impact.
102. Create your own sales advisory board group with top salespeople and talk to them and ask them questions on a regular basis.
103. Show your work! Send out a weekly update to your stakeholder teams that highlights not only good sales efforts but that also highlights the impacts made on other teams. Also, use this vehicle to highlight other teams’ contributions to the sales team.
104. The first sale is the one you make to the sales team. Convince them, and you'll have success. Fail there, and your product will flounder.
105. Avoid letting one-off requests overtake advancing the practice. Take time to prioritize how your efforts will impact the most people.
106. Make yourself available to your sales team and make sure they know you're their ally. Just as product brings the donuts with engineering, do the same with the sales team. They'll be more likely to include you on calls, share new insights with you, and provide candid feedback.
107. Measure, take regular inventories, categorize content (by product, sales stage, internal/external, messaging pillar, buyer role, etc) to help you perform a map and gap, and be in constant contact with sellers of all levels.
108. Sales are your customers. Sales enablement is like marketing to customers. You need to think at which stage of "buying" your idea or training your sales customers are and adjust your communication and message accordingly. Different sales teams, like different buyers, also have different needs and pains, therefore your message to them around the same tool or training will be different. And just like with SMM and other marketing channels, in order to keep the audience engaged, you need to "post" (communicate, train, etc.) frequently.
109. Be a tour guide and a not a travel agent, meaning you build trust when you walk the talk, i.e. do demos, speak to customers, empathize with legit sales/product frictions, challenges or weaknesses - do things that deliver value and arm the sales team which make them better in the way they see and you can measure.
110. Revenue and conversion should lead the way.
111. Listen carefully to sales requests and cross-check with customer needs.