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Sales Stack Workshop: Hacking Outbound Messaging and Cadence

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Sales Stack Workshop: Hacking Outbound Messaging and Cadence

  1. 1. Session II: Outbound Messaging and Cadence Presented by
  2. 2. Who am I? CEO and Founder, Skaled Email: jake@skaled.com Social Profile: Twitter: @JakeTDunlap @Skaledcom
  3. 3. Who am I? VP of Inside Sales and Sales Operations, DataHug Director Global Sales Operations, App Annie Senior Manager Sales Operations, Yammer
  4. 4. Who am I? Head of Product, SalesLoft Head of Sales Development, SalesLoft Recruiter, Randstad Technologies
  5. 5. Agenda Part I: Top of Funnel Technology Optimization Part III: Qualification Part II: Messaging that Converts Part IV: Handoff
  6. 6. Part I: Top of Funnel Technology
  7. 7. Top of Funnel Technology • Know your Options • Prioritize • Implement Reference: • Bowery Capital Guide to Startup Sales Tools 2.0
  8. 8. Focus: Technology that will streamline hiring, make training more efficient and comprehensive, and increase retention. • Interviewing: Take the Interview • Onboarding & Training: Grovo • Coaching & Incentives: Rivalry, Hoopla • Employee feedback: 15five, Workcompass Bowery Capital Guide to Startup Sales Tools 2.0 Manage & Grow Your Team
  9. 9. Manage & Grow Your Team Bowery Capital Guide to Startup Sales Tools 2.0
  10. 10. Bowery Capital Guide to Startup Sales Tools 2.0 Focus: Technology that allows you to automate & analyze your pipeline, providing actionable insights that enable quick data-backed decisions. CRM & Predictive: CRM: Salesforce Predictive: Infer Optimization: Operations: Insight squared, Lattice Data Management: Data entry: RingLead, Zapier Optimize Operations
  11. 11. Bowery Capital Guide to Startup Sales Tools 2.0 Optimize Operations
  12. 12. Optimize the Sales Process Focus: Technology that will streamline the sales process, and allow you to better understand and target, with more high-quality conversations. Smarketing: Social sales: Socedo Alignment: ListenLoop, Spiderbook Sales development: Lead gen: Salesloft Prospector, Datanyze Email management: Salesloft Cadence Sales: Calling: ConnectAndSell Customer success: Customer success: Gainsight Customer engagement: Skilljar Bowery Capital Guide to Startup Sales Tools 2.0
  13. 13. Optimize the Sales Process Bowery Capital Guide to Startup Sales Tools 2.0
  14. 14. ASSESS & PRIORITIZE Needs Analysis: TOF & Pipeline Diagram Lead & Technology Flow Talk to Your Team Make the Decision Selling to Leadership
  15. 15. Assessment Step 1: Needs Analysis TOF TOF: • What is our ICP? • Where are our target prospects & how do they want to be engaged? • How do we generate leads? Lead flow diagram  • VS. how do we want to generate leads? Source: ringio
  16. 16. Assessment Step 2: Needs Analysis Pipeline & Metrics Source: ringio • What does my sales cycle look like? • What type of information do our buyers consume as they move through their buying process? • What type of information do I need to report? • Tracking trends to determine what matters: Stage to stage conversion rates Average deal size Sales Cycle Opportunity Pipeline
  17. 17. Assessment Step 3: Diagram Your Technology Flow Source: ringio
  18. 18. Don’t forget: talk to your team • Use tools to streamline processes and allow reps to spend more time with prospects • Ask your team about their biggest pains
  19. 19. Discovery • Research • Resources: Bowery Startup Sales Tools • G2 crowd reviews
  20. 20. Deciding to invest What is the impact of solving the pain point? What will the project cost? How will your project disrupt existing workflows? How long before the project proves ROI? Why should we prioritize over other projects? Most importantly: Don’t make the investment in a new tool unless you’re ready to also invest in necessary training and support to maximize the tool. Source: Insight Squared Sales Ops Handbook
  21. 21. Selling to Leadership: Proving ROI
  23. 23. Consequences of Poor Training & Support Sales reps waste over 50%1 of their time every day just trying to access the tools and content needed to do their job Only 15% of sales technology purchases result in increased revenue2 1CSO Insights 2TopoHQ 3Qvidian
  24. 24. Improving Adoption FOCUS ON THE WHY Readily Available Materials • Use the sales training materials post training • Make sure tools and workflows are added to sales playbooks Build Support & Feedback Infrastructure • Make sales rep and manager interactions work • Use metrics for reinforcement
  26. 26. Conclusions • Changing buyer behavior  growing need to automate the sales process • Successful teams are already adopting tech and you can’t compete without it • You need a process to strategically decide on tech investments • Your systems & team must be agile to experiment & implement new tech • You must commit to training & support
  28. 28. Part II: Messaging that Converts
  29. 29. The Importance of Messaging 86% of the value propositions salespeople present aren’t relevant enough to get the customer to take action. (CSO Insights)
  30. 30. Messaging Best Practices • Frame your messaging thoughtfully • Keep it simple, and limit the choices and CTA • Be a challenger • Sell to the individual, then the employee, then the company CREATE EFFECTIVE MESSAGING
  31. 31. Psychology and Sales Keep it simple. “Thinking is to humans as swimming is to cats; they can do it but they’d prefer not to” Dan Kahneman, Predictably Irrational
  32. 32. Monetizing your Personas • Develop assumptions around target companies • Develop assumptions around the person • Determine the goals of the end user and the buyer • Determine the pain points of the end user and the buyer • How do we help?
  34. 34. Psychology of Messaging Do you have practical intelligence? To Sternberg, practical intelligence includes things like "knowing what to say to whom, knowing when to say it, and knowing how to say it for for maximum effect.” -Malcolm Gladwell, Outliers
  35. 35. Outbound Messaging Cadence Emails Follow up calls
  36. 36.  Subject line  Initial fact and opening ask  Giving value or knowledge  Potential fit  Ask: referral/meeting  5-7 sentences max What are the core pieces to a good email?
  37. 37. Email: tips to be successful Choose a direct subject line Time to Connect MM/DD Meeting next Thursday Quick Intro… Establish connection and give reason for contact CTA or Ask for a Referral Experience, interests, article, research or other… Outline the fit Think - Industry, Size, and Location Drop a favorable stat Close and set time to connect Use a firm ask Referral Be specific, always set up a time on a specific day Use scarcity to show value (Optional)
  38. 38. What works? • Time to meet [DATE] 35-40% • RE: Time to meet [DATE] 35%+ • Referred to you via {CFO’s First Name}’s Office 61% • Time to Connect- {!Date} 55% • Follow up from [BOSSES NAME] 40%
  39. 39. Example Email: Great Subject, Great Message Subject: Referred to you via {CFO’s First Name}’s Office Hi , I spoke to CFO's First Name's office and was pointed in your direction as the best person to discuss outsourced legal expenditures at COMPANY. To be brief, at BusyLamp we help companies like COMPANY save money by providing transparency into outsourced legal expenditures through a system of checks and balances that ensures all resources are being allocated efficiently and the end bill accurately reflects the work done. Please let me know if Thursday, April 30th at 10:00am works for an introductory phone call and I will coordinate a calendar invitation. Thanks, OPEN: 61% REPLY: 26%
  40. 40. Example Email: Great Subject, Great Message Subject: Trying to connect Hi, Hope you're having a good day. I was just researching some Boston startups and came across your company. I wanted to connect and ask if you're in need of financing at all? To be brief, we work with a number of startups and consumer goods companies that have issues securing financing; specifically companies that have sales and can't fulfill large POs; or are at the stage of growth where an influx of working capital can elevate their business to the next level. Let’s connect next week to explore if we’d be a good fit to work together. Please let me know if next Wednesday at 1:30pm works for a brief phone call and I’ll send over a calendar invite. Best, OPEN : 59% REPLY: 40%
  41. 41. Example Email: Great Subject, Great Message Subject: Time to Connect- {!Date} Hi {!First Name}, While researching companies in the {!Industry} space, I came across{!Company} and thought you’d be at a place where it’d make sense for us to have an initial conversation. At Skaled, we work hands on with growth stage companies between the Seed to Series C funding phase to help scale sales without the typical obstacles that companies tend to see during these critical stages. We have helped organizations scale and raise 100s of millions of dollars and secure customers with SMBs and Fortune 100 organizations. If scaling either your demand generation or sales efforts is something you are beginning to think through, it'd be great to have a quick chat to see how we could help. Let me know how {!Date} at {!Time} EST works for you and we can discuss your current demand generation and sales strategies to see if there could be a fit. Best, OPEN: 55.71% REPLY: 11.87%
  42. 42. Example Email: Poor Message Subject: RE: Time to Connect- {!Date} Hey {!First Name}, I just wanted to follow up on a few attempts to connect with you regarding your current sales process and lead generation efforts. We work closely with growth stage companies to help solidify their sales process early on and make that process replicable for future growth. Let me know if you are available in the next couple of weeks for a quick call. I have availability next {!Second Day}({!Second Date}) at {!Second Time}. If that works I’ll lock it down in our calendar. Best, OPEN: 55.18% REPLY: 7.23%
  43. 43. Example Email: Poor Message Re: : Time to connect Email Body Hi, I wanted to circle back from my previous email and explore whether or not ProsperWorks is a good fit for . At ProsperWorks we’re changing the way sales teams use CRMs. We’ve made the focus of our software ease of use, yet fully customizable and integratabtle with your accounting, HR, marketing and other systems. Please let me know if this coming Tuesday afternoon works for a quick phone call and I’ll coordinate a calendar invite. Best, OPEN: 39.84 REPLY: 5.42
  44. 44. Final Thoughts • We have to raise the importance of the issues first, because people buy solutions • Sales is not informing, it’s persuasion • Think narrowing your focus early on
  46. 46. Part III: Rigorous Qualification
  47. 47. Inbound vs. Outbound
  48. 48. Outbound leads Inbound leads ANUM model Authority Need Urgency Money BANT model- Budget Authority Need Timing Factors Examples and explanations Factors Examples and explanations Authority When you are talking to the decision maker, make sure to make note of what their title and function is so you can align their needs with your product. Budget The prospect tells us there is or could be a budget created for a project OR the prospect has made an enterprise software purchase sometime in the last 12 months Need Make sure to find lists of companies in the target industry you’re seeking and their size. Authority There is at least one Contact that is interested in solving its [Problem] who is Director Level or above. Also, we must have the contact info of the Decision Maker and either Acme Software or our Contact has spoken to the Decision Maker about a potential project. Urgency If a company has announced they are expanding their inside sales team or have a new vice president of sales, this could be a cue to contact them. Need We have identified a specific problem and pain point. Money If a company is growing, recently announced a round of funding, or are older, more established companies then they have the funds. Timing The prospect provides us with an understanding of a potential decision timeline, understanding of an event, or expected time of when they want a solution in place.
  49. 49. Three-part framework called GPCTBA • Asking GPCTBA questions: • Goals- what are the quantifiable goals your prospect wants or needs to hit? • Plans -what plans will they implement in order to achieve these goals? • Challenges- Can you help a prospect overcome their and their company's challenges? • Timing -When do they need to achieve their goal? • Budget- How much are they willing to invest? • Authority- Is the person you talk to the decision maker who can make the purchase?
  50. 50. Example Criteria for Qualification with “BANT” BUDGET • The company has budget set aside for your product category OR • To solve a very specific need in the business that we can help to solve for (needs must be clearly documented) - this must be verified and our product can help to achieve those needs
  51. 51. • Is the decision maker, OR • Is a key influencer and there is a defined decision making process Authority
  52. 52. Need • Has a clear need that we can help to satisfy • Has a sufficient understanding of your product • Understands what you do and technical aptitude required • Example question that gives clarity to need: “How could you see this working to help with XYZ need?”
  53. 53. Timeline • Must have an expressed business need that needs to be solved in the next six months and they are looking for a way to solve that need now
  54. 54. Part IV: Handoff
  55. 55. Handoff • Clearly define responsibilities & then experiment with those definitions • Uniform rotation system to ensure fairness • Continue to strive for alignment
  56. 56. Skaled Case Study • AEs refusing to take leads, just passing indiscriminately • Once clear need and timeline are defined they CANNOT pass • In 2 months we went from 20 per week to 20/day
  57. 57. Thank You!