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50 Sales Lessons from 3 Years in B2B SaaS

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50 Sales Lessons from 3 Years in B2B SaaS

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This deck highlights the top 50 lessons learned from my startup sales career thus far. Lessons are broken down by:

- Deal Cycles & Closing
- Sales Management
- Sales Operations
- Sales & CS Alignment

I hope you find it valuable! Thanks in advance for reading - please share your favourite soundbytes and send me any feedback you have :)

This deck highlights the top 50 lessons learned from my startup sales career thus far. Lessons are broken down by:

- Deal Cycles & Closing
- Sales Management
- Sales Operations
- Sales & CS Alignment

I hope you find it valuable! Thanks in advance for reading - please share your favourite soundbytes and send me any feedback you have :)

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50 Sales Lessons from 3 Years in B2B SaaS

  1. 1. 50 Sales Lessons from 3 Years in B2B SaaS Evan Lewis | @evanlewis_ Director of Sales, PostBeyond Inc. January 2018
  2. 2. First-Hand Lessons & Tactics from My Startup Sales Journey My first startup failed because we didn’t validate what we were building. I coded too much and didn’t really sell. I learned the hard way that sales is a crucial skill set for all entrepreneurs. Since then, I’ve spent the past 3+ years in the sales trenches, specifically in B2B Software-as-a-Service at PostBeyond. These are my top takeaways and lessons learned. I hope you find them helpful and are able to put some of the tactics to use! - Evan 3 Y E A R S , 1 0 0 0 ’ S O F M E E T I N G S & C A L L S , D I S T I L L E D I N T O 5 0 S O U N D B Y T E S
  3. 3. S A L E S O P E R AT I O N S D E A L C Y C L E S & C L O S I N G S A L E S M A N A G E M E N T P O S T- S A L E S A L I G N M E N T Core Focus Areas
  4. 4. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. Part One Deal Cycles & Closing Tactics
  5. 5. Don’t start any sales call without… 5 Probing Questions 1 Goal in Mind Stakeholder Research
  6. 6. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 6 Get excited! Smile 😃 Your positive energy rubs off on your prospects. Be polite, complimentary, and highly personal.
  7. 7. Have a pre-call routine that gets you in the right performance mindset. Personally, I stretch for 2mins" Treat each call like a sporting event where you need to perform.
  8. 8. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 8 Set an agenda at the start of each call and ask for feedback. “Is there anything I missed that you want to make sure we cover?” Credit: John Barrows
  9. 9. Multiple stakeholders on the call? Have specific questions prepared for each of them. Get them talking early, especially key decision makers. Go out of your way to show that you’ve done your research and you respect their time.
  10. 10. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 10 Ask concise, one-sentence questions. Avoid the temptation to lump multiple questions into one jumbled thought. Write your individual questions down ahead of time. Practice your delivery.
  11. 11. After you ask a question, learn to love silence. 🤫 Cherish it. Let it simmer.
  12. 12. Video works. Period. Put yourself on camera. You’ll build stronger relationships, guaranteed. Products To Check Out: Vidyard, Zoom
  13. 13. Build some healthy skepticism into your sales approach. People will waste your time if you let them. Hold buyers accountable to their commitments. If they don’t follow through, they likely aren’t real.
  14. 14. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 14 With every customer touchpoint, use one simple question to guide you: “Am I adding value?” If not, go find some. Don’t just follow-up.
  15. 15. Kill the phrase “following up” from your vocabulary. Continue the conversation instead. Credit: John Barrows
  16. 16. Avoid just “sending more information” when you can. When you do, use analytics to understand your prospect’s intent. Products To Check Out: LinkedIn PointDrive, SalesLoft, GoVideo
  17. 17. In every deal, ask yourself: “Do I have an ally or mobilizer on the inside?” Ally / Mobilizer (n): Someone who pushes the deal forward, gives you the inside scoop on stakeholders and lays out the steps you need to take to win. Your deal cycles will be shorter for it.
  18. 18. Having trouble getting up the chain to decision makers? Ask your prospect about them. “Have you talked to X about this project? What was his/her feedback?”
  19. 19. Make it easy for your prospects to buy. Build a business case that they feel confident selling internally. 💼 Business Case Components ✅ 1. Customer Pain To Be Solved 2. Program Objectives 3. Technology Overview 4. KPIs / Success Measurement 5. Stakeholders Involved 6. Implementation Plan + Timeline 7. Case Study w/ Similar Customer 8. Pricing & Scope 9. ROI Breakdown
  20. 20. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 20 Always anchor your business case to the customer pain 🤒 Get the prospect to answer these questions LIVE on a call while you play scribe: 1) The problem we are aiming to solve is… 2) This problem is stopping us from hitting our goal of…. 3) This problem is a priority now because… 2) If we do not solve this problem now, we will…
  21. 21. If a buyer doesn’t grant you access to meet with other stakeholders who need to be involved, they likely aren’t serious about doing a deal.
  22. 22. If your prospect… 1) Looks nothing like your existing successful customers (industry, size, use-case, persona) 2) Is saying all the right things and insists they can move quickly and skip steps in your sales process …you shouldn’t count on them closing.
  23. 23. Strive to have a VP-level champion or above in every deal. Watch your deal cycles shrink!
  24. 24. Avoid letting weak champions sell on your behalf. Ask to be in the room 💬 If their boss picks holes and you aren’t there to push back, you’re going to lose.
  25. 25. ☎ Dial at off-times of day ⏰ Catch people when they have a free minute – 5:30-6:30pm on the drive home usually works well.
  26. 26. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 26 Need more intel on where you stand in a deal and what you can do to help? Use unconventional channels to communicate with stakeholders. Friendly Twitter DMs, texts and LinkedIn messages are 👌
  27. 27. Sticky situation on an email thread? Unclear of what the prospect means? Pick up the phone!!! It is easier to talk it out live than to wordsmith and hope for the best.
  28. 28. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 28 When talking about price, have a frame of reference for what your prospect could spend. Use other technologies or services they have purchased as benchmarks. Never price low out of the gate if you don’t need to.
  29. 29. Practice your pricing delivery. Be as frank, clear and nonchalant as possible. Credit: Chad McCaffrey
  30. 30. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 30 Learn your buyer’s fiscal year-end. Ask if they have discretionary budget mid-fiscal. Prioritize your pipeline accordingly. As much as you want to, you can’t force people to buy when the money simply isn’t there.
  31. 31. Lay out your next steps. Be prescriptive. Help the buyer understand why the next step will be helpful for them.
  32. 32. Always have levers you can pull in negotiation. Think ahead and chart your Gives and Gets. Credit: Taylor Coulis
  33. 33. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 33 Get confirmation on pricing boundaries from your boss. It helps with your confidence and delivery when you are 100% sure what your options are.
  34. 34. Play the man behind you. When it comes to holding firm on deal terms, make your boss the bad guy. Credit: Chad McCaffrey
  35. 35. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 35 Anticipate roadblocks or slowdowns in your deal cycle. Ask your champion for permission to get ahead of them. Common Slowdowns: - IT evaluation - Security questionnaire - Legal MSA review
  36. 36. Stalled deal? Call-outs work 📣 If prospects aren’t delivering on their commitments, don’t be afraid to call them out politely. If they can’t handle the truth and own up, you know you don’t have a real champion.
  37. 37. Think like a marketer. As a salesperson, your personal brand matters. Prioritize creating original content to establish your voice.
  38. 38. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 38 Make time for social 📲 Build a social selling routine that fits with your schedule, and stick to it.
  39. 39. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. Part Two Sales Management
  40. 40. Recruit and screen new hires against clear success criteria. Don’t hire for the sake of hiring. Set the bar high and keep it there. Credit: Kyle Norton
  41. 41. Pipeline is precious. Before passing deals to new reps, do your best to certify them. Run them through mock deal cycles with coaching throughout.
  42. 42. Your team is a reflection of you and your attitude. Bring the energy and positivity, every single day. Credit: Kyle Norton
  43. 43. Prove you can get new reps to productivity & quota attainment before hiring in bulk. It is better to have a few reps getting FAT than many who are starving.
  44. 44. Build call recording and coaching into your sales culture. Circulate recordings with your marketing and leadership teams to help everyone understand buyer behaviour and pain.
  45. 45. Make a habit of deconstructing Closed/Lost and Closed/Won deals. Look for patterns. Fill the glaring gaps and double down on what’s working.
  46. 46. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 46 Make clear asks of marketing. Their job is to make sales easier. Hold them accountable. Better yet, collaborate!
  47. 47. Small and frequent SPIFs are helpful. Make it easy for your reps to feel like they are winning.
  48. 48. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. Part Three Sales Operations
  49. 49. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 49 Prioritize your Salesforce hygiene from Day One. Opportunity records should be sacred and have strict rules for upkeep.
  50. 50. Track days in stage and diagnose what a “good” deal looks like 📆 ie. Discovery – 10 days, Evaluation – 30 days If a deal is taking longer in a specific stage, that is a good trigger to dive in and understand why. Credit: Randy DeHaan Product to check out: InsightSquared
  51. 51. Track revenue per lead. It will help you understand sales efficiency.
  52. 52. Map your buyer’s journey end to end. Set your Salesforce stages to align with key milestones in their journey. Image Credit: Jacco van der Kooij
  53. 53. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 53 Depending on your stage, consider what is more important to you – revenue or logos? Set your pricing strategy accordingly. Make sure you aren’t pricing yourself out of conversations with logos you’d love to have.
  54. 54. When it comes to target industries, less is more to start with. Prove that you can own ONE first, then broaden your reach.
  55. 55. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. Part Four Sales Alignment with Customer Success
  56. 56. © PostBeyond Inc. Strictly Confidential. Do Not Distribute. 56 Be diligent about mapping your post-sale handoff process. Make sure that expectations are clear for the AE and the CSM.
  57. 57. As a sales rep, stay close to your champions and closed deals. Nurture those relationships and keep tabs on how the customer is doing with your product. If they aren’t seeing success and you haven’t kept in touch, they will be at risk of churn.
  58. 58. Thank you for reading! Let’s keep in touch. ü Tweet @evanlewis_ ü Add me on LinkedIn ü Email evan@postbeyond.com

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