The Sales Development Playbook

Book 15 of 52 in the Mitch’s Notes Project

Why This Book

We know that the best products do not always win. (22 Immutable Laws, Different) The product with the best go-to-market distribution model does. (Content Trap, 20 Principles) And that difference can be a competitive moat that creates monopoly profits. (Zero to One) When building a startup, go-to-market fit matters as much as product-market fit.

We covered the enterprise sales motion in The New Strategic Selling. This book is about a specific role in an inside sales motion. However, the book also covers broader inside sales topics and serves as a checklist for many other sales and broader corporate development best practices in recruiting, retention, execution, and leadership.

What is In It For You

If you’re a CEO or if you run a department of sales or marketing, you may be wondering how you can accelerate revenue growth from so-so to stellar. I’m sure you have a fantastic product and great sales team, but perhaps there just isn’t enough activity at the top of the funnel.

The author believes that Sales Development, a specialized role focused on the frontend of the sales process — qualifying inbound leads and/or conducting outbound prospecting — to generate sales pipeline, is the answer to this top of the funnel problem.

Sales Development Elements

According tot he author, here is what is in it for you:

Part 1: Strategy shares a framework for thinking about how to align your sales development model with your specific market dynamics and buyer’s journey. After reading part 1, you’ll have the criteria to determine your model and be fully versed in the critical success factors.

Part 2: Specialization presents stories of innovative companies applying new thinking and taking their groups to the next level. You’ll learn about segmenting your prospect universe, specializing roles, and how it all comes together.

In Part 3: Recruiting roadmap for hiring with urgency and attracting top talent. Recruiting tactics, compensation, and a hiring process are presented in great detail.

Part 4: Retention goes deep on the stuff that never seems to get enough consideration: engaging, developing, and motivating people. These chapters are filled with actionable advice on everything from coaching to building career paths.

In Part 5: Execution strategies and examples for onboarding, crafting buyer-based messaging, and designing effective outreach. You’ll get dozens of ideas on everything from methodology to creating amazing voicemail and email messages.

And finally, Part 6: Leadership gives actionable advice on what it takes to lead sales development today. There’s a lot to learn about quota setting, measuring what matters, and acceleration technologies, so those are covered in depth.

Where Should you Start

There are role definitions that will help you match those discussed here with those you use in your organization.

● Sales development reps (or SDRs) are responsible for the front end of the sales process. They either set introductory meetings or generate qualified opportunities for sales partners.

● Inbound sales development reps (often called BDRs, LDRs, or similar) are responsible for inbound lead qualification in response to marketing programs.

● Outbound sales development reps (often called ADRs, MDRs, or similar) are responsible for outbound prospecting.

● Account executives carry a revenue quota. Also called territory managers, sales executives, or similar, they convert opportunities into closed business. For our purposes, this can include inside (phone-based) or field (road-warrior) sales reps.

This book is 234 pages long and has a whopping 37 chapters. On average the chapters are only 6.3 pages long. That means we can boil down each chapter into a single paragraph. It also means that the chapter headings themselves provide a checklist for sales development. So, start with the table of contents and dive deeper into the chapter summaries that pique your interest.

You should buy the book, although not necessarily from Amazon

Part I: Strategy

1. Selling in the 21st Century

The companies that win today are those that are willing to reach out, stand out, and point out flaws in status quo thinking. Your prospects are primarily concerned with how you can help them build a better business. Selling isn’t interruption or trickery. It is, at its heart, about service.

The value of a sales development effort is measured by increased won business per account executive and/or accelerated new customer acquisition.

2. Consider the Five Whys

The final three whys (Change, You, and Now) are about gaining commitment and closing a sale. They are the domain of account executives, and, as such, we won’t be discussing them further. But take another look at the first two whys (Listen and Care). These two are about opening doors and sparking interest.

Why listen and why care are the domain of sales development.

3. Let Requirements Guide Your Model

A good sales development team adds value from day one. It is up to you to understand the value of the conversations they’re having, to quantify that pre-pipeline value, and to communicate it across your organization. What did they cost? And What did they yield? are important questions. But they are not the end-all for fledgling groups. Sales development is an investment, not a cost center. Embrace that fact, and you are well on your way to setting realistic expectations.

Effective sales development means maximizing the productivity of both the SDR and the AE teams. There are two main models in play: setting introductory meetings and generating qualified opportunities.

You should deploy an introductory meeting model when the market for your product is immature and/or when your account executives need more at-bats.

If your market is mature, you should use qualification. The author created an acronym to develop the qualification process. PACT: pain, authority, consequence, target profile, and timing.

Part II: Specialization

5. Go Allbound for Pipeline

Its not inbound or outboand, it is all bound, you are going to have to use both because at the very highest (see chart below) not even half of your closed deals will be sourced from marketing efforts.

Those numbers are only as high as they are because those companies actually have a marketing function, which as we have talked about in several other book reviews, is often rare in startups.

The best way I can put it is that the “cold calling is dead” camp is half right. In reality, it’s the cold that’s dead, not the calling.

Ken shared that an inbound opportunity is roughly twice as valuable as one generated through outbound effort. But the challenge — and it’s a big one — is that there are exponentially more small companies than big ones. As a result, the vast majority of inbound leads are small. “If you want to go upmarket, which you absolutely must if you want to grow, you have to go outbound,” shared Ken. “Since inbound is worth twice as much as outbound, I say go after accounts twice as big when you go outbound.

6. Sell to Everyone; Close No One

This is a key theme touched on in the marketing books and the sales books as well. You have to know your ideal customers. You have to know the red flags that lead to dead ends. You have to know your customer before you can map how to solve their problems. This book provides an easy to remember ABCD framework to help you segment leads.

Segment your customers and leads by traits using your ABCD’s

7. Specialize to Accelerate

“The right coverage model, aligned to your strategy, maximizes your chances of turning prospects into customers.” VP of Inside Sales at CA Technologies.

Once you hit more than 4ish reps, you can start using them to specialize between inbound and outbound SDR’s. Here are the most important factors to the authors.

If you have a marketing machine that is churning out quality leads and you are looking to ramp your team you should know how many leads a rep can handle. It differs between inbound and outbound SDRs:

1. Inbound SDR: 200–300 lead per month
2. Outbound SDR: 100–200 cumulative leads

8. Consider the Research Role

I think that more organizations, including my own, would benefit from a research athlete. Someone whose role it is to ensure data hygiene and to provide bespoke insights about prospects. How can you measure the ROI on a role like this?

Nearly one-fifth of rep time was spent reviewing target account quarterly earnings calls for “nuggets” to use in their prospecting. These sales triggers made for highly effective sales messaging, but they took significant time to uncover.

If a researcher can support a team of 5 SDR’s, that researcher will be equivalent to hiring another outbound SDR. The per call sales efficiency would be an interest metric to know what ROI exists on top of the time savings.

When should you hire a researcher?

• You have a dedicated outbound SDR team.
• Your reps are juggling multiple tools to build account and contact lists.
• The profiling data that separate an A-List account from a Dead End isn’t easy (or cost effective) to lay hands on.
• Your reps are spending significant time identifying relevant research points.
• Your reps are calling into popular titles and need deep research to stand out. !)

9. Follow the Early Adopters

If speed to contact is your goal, you need a specialized inbound team. Territories, routing, process, and handoff all need to be oriented toward immediate follow-up. It is difficult to balance meeting SLA commitments with marketing while also giving reps the latitude to decide who/who not to call.

Part III: Recruiting

10. Hire with Urgency

Just as go-to-market is as important as product / market fit, so too is sales rep recruiting as important as engineer recruiting. It can be a strategic advantage over your competitors and will lead to your own job security!

“I came to the conclusion that hiring had to be my number one priority,” commented Mark [Roberge, CRO at Hubspot]. “I felt that if I could get the right people into the system, even if I did a mediocre job at training and management, they would find a way to win. But if I got mediocre people in, even if I did a world-class job at training and leading, it wouldn’t matter.”

When you are launching SDR’s hire them in groups of at least 3. Hiring in groups is vastly more efficient because onboarding is simplified, your time is protected, and your new hires bond together. If one or two reps don’t pan out, at least you aren’t starting from zero.

When it comes time to scale, you need to know that your process is repeatable and that your message is on point. Whenever possible, plan to hire in groups. You’ll learn a ton along the way, and you’ll be better prepared for hiring and onboarding your next class of reps.

11. Spot Qualities of Qualified Candidates

Profiles you should be looking for in SDRs.

• Recent university graduates
• Experienced SDRs
• Military to civilian transitions
• Job shifting professionals trying to break into sales

Characteristics you should be looking for in an SDR [or any startup hire]

There are three characteristics that are universal in the best sales development candidates: passion, competitiveness, and curiosity.

Passion — perseverance and grit over the long term.

Interview question: What’s something you’re obsessed with right now?

Competitiveness — compassionate competitors that like to win, but not at the expense of their teammates.

Interview question: Would you rather be the #1 rep while the team misses the number? Or be #2 while the team hits the goal?

Curiosity — reps who are intellectually curious lifelong learners and who strive to figure out what works and try new things.

Interview question: What is the last book you read? In prepping for this interview, what surprised you about our company?

12. Write Job Descriptions, Not Sleep Prescriptions

A job description should sell the job. If you can’t capture attention and interest, who the hell cares about the fine print

Job descriptions should leave candidates with just one impression: this is the place to advance my career

It isn’t a laundry list of job duties, but rather it paints a picture of how the candidate will learn and grow in the position.

Is it easy to write a killer job description? No, but it is the face you put forth to the market. Consider it a piece of content that is used in the sales process. The person you are selling to is the potential candidate.

13. Compensate at Market Rate

This book was originally published in 2016. When the book went to print the author’s estimate of SDR compensation can be found in the first table. I adjusted these numbers for inflation to attempt to convert them to 2019 numbers, but as the author points out there are several other factors that affect compensation in your specific geographies.

The most important factors in compensation are as follows:

1. Region — Pacific Coast, Mountain, Mid-West, Northeast, etc.
2. Required sales experience — none, less than 1, 1+, etc.
3. Model — introductory meets vs. qualified opportunities
4. Average sales price — <$10K, $10–49K, $50–99K, etc.
5. Product type — SaaS, on prem, service, product, etc.

The author has a fantastic compensation calculator you can download here: LINK .

14. Build Attractive Compensation Plans

Just like the Navy SEALs value simplicity in their orders, so too do your reps. Good compensation plans accomplish three things:

1. Clarity — no more than two moving pieces and is easy to understand
2. Commissions — rewards must be paid promptly. The sooner the better. For a coin-operated sales force, prompt payment can be a differentiator.
3. Control — Reps must control their own destinies, meaning they can’t be comped on things outside of their control.

There are two options for comping SDRs: 1. Pay on Meetings. 2. Pay on Qualified Opportunities. Here are proposed plans for each option:

If you are worried about SDRs setting meetings with the wrong prospects, you need to realign your right profile, right person, right pain criteria.

The accelerators for the meeting model are important to create the incentive for over-performance.

The opps won % should never be above 20% because the reps do not control their own destiny.

15. Source Candidates Effectively

Hiring green candidates is all about relationships with the local universities to get in before career day, creating a great job posting, and an intern pipeline.

Hiring experienced candidates is about the tactics:

1. LinkedIn + Messenger (CEO, SVP Sales, Sales Manager, etc.) + Ask (For a conversation, not a resume)
2. Prompting Employee Referrals — manager should go through reps connections to identify potential referrals and discuss with the rep.
3. Setting a Networking Quota — have a hiring meeting x times a day/week/month whether or not you have an open req.

16. Glassdoor Like a Pro

Glassdoor has 3 key metrics. As a benchmark, you should be shooting for at least a 3.7 out of 5 starts and 80%+ in recommend to a friend, and approve of the CEO. A great Glassdoor profile with videos about the company, real employee pictures, highlighting core values, and lots of employee reviews is key. Making sure that those reviews are honest is also important. You do this, not by providing a template and mandating that people share, but by encouraging people that if they love their job and are excited about the company, Glassdoor is a good place to share.

17. Treat Hiring Like a Sales Process

1. Application and Survey —the survey in particular is an interesting test for SDRs to do some web scraping (essentially the job they are applying for) as a gating process.
2. SDRs make their living on the phone. This is the HR reps job to gather basic information about the candidate and assess how well they handle conversations over the phone.
3. Candidates need to be prepared. Questions like what do you know about the company? What do you know about me personally? Are both great questions to show motivation and preparedness.
4. One piece of advice I liked here was that the candidate is judging you and your organization as well. This is a chance to sell the culture and opportunity. Also, look for the candidate that “close” the interview.
5. Allowing the candidate to ask the SDR questions (and they should ask prepared, pointed questions) about the role will help them understand what the opportunity really looks like.
6. Take a look at some of the most highly rated employers on Glassdoor, and you’ll notice a common thread: their interview processes are lean. Many run from soup to nuts in just two weeks. If you want your perfect candidate to choose you, you need to move quickly.

Part IV: Retention

18. Lead Your People

The single biggest factor that drives SDR retention is the person managing the team.

Today, reps expect a learning culture, they expect to grow professionally, and they expect you to deliver in those areas. The best leaders live by the following: My top priority is to increase the skills of each rep and the performance of my team. To do that, I’m going to create a robust learning environment. I commit to growing the talent of those I lead and to ensuring they remain within the company as valuable contributors.

Here are some other factors that drive retention.

19. Prioritize Coaching

Coaching is not a component within the sales manager role; managing is now a component of the new coaching role.

To my mind, sales training is about teaching a new technique or idea. Sales coaching is about returning to a topic that is “old hat” and elevating a rep’s abilities higher and higher, incrementally. The only way to make coaching a priority is to make the case with numbers. Only by demonstrating that an hour spent coaching has a higher return on investment (ROI) than an hour spent poring over metrics — or lost in yet another meeting — can we make room for coaching. Making sales coaching a priority is a business decision. Coaching improves retention and performance. Those are tangible business outcomes that even the shrewdest CFO can’t argue against.

Good example for connecting coaching to the bottom line

20. Coach to Improve

1. Define the commitment — call your shot and use others to hold you accountable
2. Create a schedule — If you don’t calendar the coaching it won’t get done
3. Measure results — track how you’re doing against commitment
4. Keep it fun — mix up the type of training and create a culture of continuous improvement.

• Recorded calls — make sure you are compliant with regulations, but recorded calls are gold mines.
• Side-by-side coaching — See how the reps work their lists, prepare for calls, how effectively they’re using the tools and technologies at their disposal.
• Group sessions — Teach the entire team, have a call hall of fame.
• Self-assessments — Reps need to interested in constant improvement. Let them measure themselves against themselves over time.
• Hot seat — do it yourself. Be the person that can say “I know this works because I’ve tested it.”

21. Develop to Grow

Coaching is important for retention, performance, and culture. This is about exposing your reps to other parts of the company, developing their skills, and give back to the team.

1. Meet — Meeting is about getting exposure to other parts of your company.
2. Learn — Learning involves your reps studying to become more well-rounded professionals.
3. Teach — Teaching requires reps to understand ideas so deeply that they are able to present them to others.

22. Build Career Paths

There is a disconnect between SDR exceptions and management expectations. It begins at the hiring date when SDRs are over-promised in order to close them.

If your SDRs want to become closers here are some proposed career paths depending on ASP size.

If your SDRs want to transition to a different team, here are some proposed career paths

Part V: Execution

23. Master Blocking & Tackling

The visual below has one point, you have to onboard your reps.

Reps learn best when the information is chunked, sequenced, and connected.

1. CHUNKING— It’s easier to learn a new subject in bite-sized chunks. When you overwhelm someone, information isn’t readily absorbed.
2. SEQUENCING: Determining what comes first, in order of importance, is key to learning (think: logical building block).
3. CONNECTING: This ties it all together. You’ve created a learning sequence built with bite-sized chunks of information. Now you need to connect the dots.

Keep onboarding sessions short. Make the order purposeful. Let them sleep on it. Learn, then do. Revisit. And revisit again. This is how people learn.

24. Onboard by a Process, Not an Event

1. Tell them why before what — If you teach reps about our products before they understand their problem, future conversations will be about products and not about the urgency of solving the problem.
2. Leverage Internal Prospects — The point is that every company has a big, hairy vision for changing the world. But can most reps clearly articulate it? Probably not. Spending time with a senior manager to gain an understanding of why your company does what it does can be very motivating.
3. Exit the Bubble — If your reps never exit the sales development bubble, they won’t have the full picture of what it is that your company does.
4. There Will Be a Test — Create a certification test
5. Be Prepared to Break Some Eggs — It doesn’t go crawl, walk, run. It goes fall, crawl, face plant, walk, stumble, run. Expect to screw up. Yes, it’ll be humiliating, but you’ll forget it in no time.

25. Create Compelling Conversations

Suspend your ego to get people to like you. This requires actually being interested in prospects. Reps need to be fully fluent in prospect challenges, motivations, and status quos. In short, they need to use buyer-based messaging.

Buyer-Based Messaging — Differentiate themselves with messages unique to each prospect. Speak directly to prospect concerns, priorities, drivers, and levers. Generate curiosity versus sounding like “just another sales rep”

In the New Strategic Selling, we discussed the need to map what a win is for each type of buyer. This book adds incrementally to that framework with the prospect persona:

26. Architect Your Outreach

Effective outreach means mastering two things: a multi-touch cadence and a multimedia approach.

27. Normalize Your Cadence

The authors gave SalesLoft’s SDR 7 touch in 7 days outreach cadence:

DAY 1- Reps send a personalized email in the morning. Later that day, they’ll reach out via phone and either connect with the prospect or leave a voicemail.

DAY 2- It’s a phone call with no voicemail.

DAY 3- Another call with voicemail in the morning and then one more call in the afternoon without voice mail. So in the first 3 days, we’ve got 1 email, 2 voicemails, and 2 no-voicemails.

DAY 4- It’s another email. DAY 7- Reps sends a final email and try to be original and human. SalesLoft has found humor to be very effective in this touch.

28. Instill a Love of Voicemail

But voicemails that are targeted, state a reason for the call, and share relevant information work big time.

1. Be Different and Be Relevant — Be interesting, relevant, and human.

2. Be Specific with A Strong Ask — Don’t hope to get some time, ask directly for what you want.

3. Don’t Reference Previous Attempts — Don’t follow-up or check in

4. Don’t Trick Prospects — Don’t be misleading

Conventional wisdom tells us that the average prospect spends eight to fifteen seconds before deciding whether to continue listening or delete a voicemail. That’s a very short runway to be different, be relevant, and interrupt the pattern.

29. Engage with Email

Good emails come in three paragraphs:

1. THE OPEN: If you don’t hook them with the open, it doesn’t matter how well you execute the next two paragraphs. “An opening line addressing a relevant problem tends to grab my attention. Something straightforward and human.”
2. THE WIIFM: What is in it for them? The key is to get to the point succinctly, with personalization, and speak to a specific professional challenge.
3. THE ASK: This is the call to action. If the ask is clear and simple, the likelihood of responses increases exponentially. If confusing or requiring too much work, they won’t.

Part VI: Leadership

30. Choose the Right Captain

The companies we work with are usually somewhere between hiring a Director and a Manager. There is usually some question as to what the Director’s role should be or whether they have the right guy in the seat. There are two quotes in this chapter that really resonated with me:

If you’re a senior executive with other responsibilities, do yourself a favor and invest in hiring the level of leader you need. Hand it over to someone who has the know-how and the passion for it.

A director is someone who can interpret results and make course corrections — someone with experience who can take the overall goals delivered by the executive team and drive results. Directors have been here before. They’ve taken their lumps and are armed with the knowledge and experience that lets them hit the ground running.

The take-away is: the VP of Sales can be your best friend if they have the experience, knowledge, and ability to drive results. Go find that person for your organization.

31. Equip the Team

You should create toolkits and playbooks to onboard your reps efficiently. It should have the following sections:

1. Understand/target — knowing your customers, their personas, and what constitutes a win for them
2. Strategize/plan — this is where your qualification criteria, sample questions, PACT: Pain, Authority, Consequence, Target Profile, and map the handoff.
3. Contact — multi-touch cadence, and multimedia approach.
4. Message — Messaging by persona, customer stories, hall of fame for emails, VMs, etc.
5. Overcome — playbooks for pushback and battlecards for competition
6. Execute — Quota, compensation, activity metrics, and anything else needed to execute.

32. Set Appropriate Quotas

Setting goals is about balancing interests: CEO — revenue growth, productivity; CFO — cost of sales; VP of Sales — team morale and retention; Reps — earnings potential and culture / climate.

Therefore, an ideal quota program will deliver results that look like these: Team goal reached, 65% of reps attain quota. There are various consideration you should make in setting quota.

1. ACTIVITY FOCUS: Is your team qualifying inbound leads or conducting outbound prospecting?
2. MODEL: Are you closing on interest? Or qualifying for need? Closing on an introductory meeting is much easier than fully qualifying an opportunity.
3. SIZE OF ACCOUNTS: What size of company and what level within an organization are you targeting?
4. MARKET MATURITY: Are you selling into a mature market (where the need is understood) or immature (where the concept itself is new)?
5. REP TENURE: Are your reps fully ramped? Should you provide those reps with a different quota?

33. Build Your Process

Great process is the foundation for repeatable, scalable success. High-performing organizations are twice as likely as underperforming ones to be process-driven.

The four processes that SDR leaders should own are:

1. Cadence and media — See Chapter 27
2. Speed-to-contact — 10x more likely to contact and 6x to qualify if they call in the first hour. Remember not all leads are created equally, so treat them differently. If speed is important then pre-set plays for the persona should be used.
3. Account-centric prospecting — Don’t process leads, prospect accounts. When a (lower-level) contact takes some action, yes, your reps should follow up. Then, either at the same time or subsequently, they should reach out to a higher-level contact too.
4. The SDR-to-account executive handoff — See Chapter 34

34. Perfect the Handoff

There are 5 steps in the handoff process:

1. Agreement on what is a valid appointment — Ensure that there is qualification, set the call objective, outline the account profile, gather the contact information, and set the acceptance criteria.
2. Before the call — Effective handoff requires calendaring a meeting, introducing all parties, communicating next steps, and setting an agenda for the discovery call.
3. During the call — SDRs should make introductions, listen as a part of training, and silently communicate with the AE if necessary.
4. After the call — Immediate debrief on how well the call went, what they could have done better, is it a real opportunity, if not, why not?
5. Future proofing — a cross functional team of engaged reps will ensure that the best ideas get shared and implemented

35. Measure What Matters

The biggest impact comes from understanding the difference between the piles of data and the information and insights that help make decisions and affect the performance of your team.

36. Manage with Meaningful Metrics

Activity metrics — “Informing your reps that x activities will lead to y outcomes and drive z results is real leadership.” Your job is to find out what those metrics are.

Objectives — Connects and quality conversations, conversation rates, email response rates, bad data / no fit rates

Results — Accepted opportunities, show/no show rates, sourced pipeline and won business.

Dashboard — shows meaningful metrics, in a specified timeframe, to a specific audience.

37. Enable with Technologies

The technologies you implement for your team are critical. Great technology implemented well has the potential to accelerate excellence. The wrong technology, no matter how well implemented, has the potential to accelerate “suck.”

1. Category 1: Account and Contact Data — accurate names, titles, email addresses, and direct-dial phone numbers
2. Category 2: Sales Intelligence — high value research tools
3. Category 3: Dialing Platform — automated dialers.
4. Category 4: Email Platform — send later, reminders, templates, mail merge, attachment analytics, insert calendar.