1. Session II: Outbound
Messaging and Cadence
Presented by

2. Who am I?
CEO and Founder, Skaled
Email: jake@skaled.com
Social Profile:
Twitter:
@JakeTDunlap
@Skaledcom

3. Who am I?
VP of Inside Sales and Sales Operations,
DataHug
Director Global Sales Operations, App Annie
Senior Manager Sales Operations, Yammer

4. Who am I?
Head of Product, SalesLoft
Head of Sales Development, SalesLoft
Recruiter, Randstad Technologies

5. Agenda
Part I: Top of Funnel Technology Optimization
Part III: Qualification
Part II: Messaging that Converts
Part IV: Handoff

6. Part I: Top of Funnel Technology

7. Top of Funnel Technology
• Know your Options
• Prioritize
• Implement
Reference:
• Bowery Capital Guide to Startup
Sales Tools 2.0

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. Manage & Grow Your Team
Bowery Capital Guide to Startup Sales Tools 2.0

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. Bowery Capital Guide to Startup Sales Tools 2.0
Optimize Operations

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. Optimize the Sales Process
Bowery Capital Guide to Startup Sales Tools 2.0

14. ASSESS & PRIORITIZE
Needs Analysis: TOF & Pipeline
Diagram Lead & Technology Flow
Talk to Your Team
Make the Decision
Selling to Leadership

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. 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. Assessment Step 3:
Diagram Your Technology Flow
Source: ringio

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. Discovery
• Research
• Resources: Bowery Startup Sales
Tools
• G2 crowd reviews

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. Selling to Leadership:
Proving ROI

22. IMPLEMENTATION & TRAINING

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. 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

25. PREPPING FOR THE FUTURE

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

27. WORKSHOP I:
TECHNOLOGY
OPTIMIZATION

28. Part II: Messaging that Converts

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. 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. 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. 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?

33. CONVERT TO MEETINGS

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. Outbound Messaging
Cadence
Emails
Follow up calls

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. 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. 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. 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. 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. 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. 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. 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. 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

45. WORKSHOP II:
MESSAGING &
ROLE PLAYS

46. Part III: Rigorous Qualification

47. Inbound vs. Outbound

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. 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. 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. • Is the decision maker, OR
• Is a key influencer and there is a
defined decision making process
Authority

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. 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. Part IV: Handoff

55. Handoff
• Clearly define responsibilities & then
experiment with those definitions
• Uniform rotation system to ensure
fairness
• Continue to strive for alignment

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. Thank You!