Session II: Outbound Messaging and Cadence

Presented by

Who am I?

CEO and Founder, Skaled

Email: jake@skaled.com Social Profile:

Twitter: @JakeTDunlap@Skaledcom

Who am I?

VP of Inside Sales and Sales Operations, DataHug

Director Global Sales Operations, App Annie

Senior Manager Sales Operations, Yammer

Who am I?

Head of Product, SalesLoft

Head of Sales Development, SalesLoft

Recruiter, Randstad Technologies

AgendaPart I: Top of Funnel Technology

Optimization

Part III: Qualification

Part II: Messaging that Converts

Part IV: Handoff

Part I: Top of Funnel Technology

Top of Funnel Technology

• Know your Options

• Prioritize

• Implement

Reference:

• Bowery Capital Guide to Startup Sales Tools 2.0

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

Manage & Grow Your Team

Bowery Capital Guide to Startup Sales Tools 2.0

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: SalesforcePredictive: Infer

Optimization: Operations: Insight squared,

LatticeData Management:

Data entry: RingLead, Zapier

Optimize Operations

Bowery Capital Guide to Startup Sales Tools 2.0

Optimize Operations

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: SocedoAlignment: ListenLoop,

SpiderbookSales development:

Lead gen: Salesloft Prospector, Datanyze

Email management: Salesloft

CadenceSales:

Calling: ConnectAndSellCustomer success:

Customer success: GainsightCustomer engagement: Skilljar

Bowery Capital Guide to Startup Sales Tools 2.0

Optimize the Sales Process

Bowery Capital Guide to Startup Sales Tools 2.0

ASSESS & PRIORITIZE

Needs Analysis: TOF & PipelineDiagram Lead & Technology Flow

Talk to Your TeamMake the Decision

Selling to Leadership

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

Assessment Step 2: Needs AnalysisPipeline & 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 ratesAverage deal sizeSales CycleOpportunity Pipeline

Assessment Step 3: Diagram Your Technology Flow

Source: ringio

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

Discovery

• Research• Resources: Bowery Startup Sales

Tools• G2 crowd reviews

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

Selling to Leadership:Proving ROI

IMPLEMENTATION & TRAINING

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 Insights2TopoHQ3Qvidian

Improving Adoption

FOCUS ON THE WHYReadily 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

PREPPING FOR THE FUTURE

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

WORKSHOP I:TECHNOLOGY OPTIMIZATION

Part II: Messaging that Converts

The Importance of Messaging

86% of the value propositions salespeople present aren’t relevant enough to get the customer to take action.

(CSO Insights)

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

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

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?

CONVERT TO MEETINGS

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

Outbound Messaging

CadenceEmails

Follow up calls

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?

Email: tips to be successfulChoose a direct subject line

Time to Connect MM/DDMeeting next ThursdayQuick Intro…

Establish connection and give reason for contact CTA or Ask for a ReferralExperience, interests, article, research

or other…

Outline the fitThink - Industry, Size, and LocationDrop a favorable stat

Close and set time to connectUse a firm askReferralBe specific, always set up a time on a

specific dayUse scarcity to show value (Optional)

What works?• Time to meet [DATE]

35-40%

• RE: Time to meet [DATE]35%+

• Referred to you via {CFO’s First Name}’s Office61%

• Time to Connect- {!Date}55%

• Follow up from [BOSSES NAME]40%

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%

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%

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%

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%

Example Email: Poor Message

Re: : Time to connectEmail BodyHi,

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

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

WORKSHOP II:MESSAGING &

ROLE PLAYS

Part III: Rigorous Qualification

Inbound vs. Outbound

Outbound leads Inbound leadsANUM model Authority Need Urgency Money BANT model- Budget Authority Need TimingFactors 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.

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?

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

• Is the decision maker, OR

• Is a key influencer and there is a defined decision making process

Authority

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?”

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

Part IV: Handoff

Handoff

• Clearly define responsibilities & then experiment with those definitions

• Uniform rotation system to ensure fairness

• Continue to strive for alignment

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

Thank You!