Sales Leader’s Guide to
Introduction by TK 01
How We Wrote This Book 02
Challenge #1: Inconsistency in the Sales Process 03
Challenge #2: Lack of Pipeline to Hit Your Number 07
Challenge #3: Rep Productivity 12
Challenge #4: Lack of Visibility 16
Why You Need a Sales Success Platform 19
Sales leadership has always been a tough job. Today, in addition to managing the
interpersonal dynamics of a team, Sales Leaders are having to navigate an increasingly
complex B2B buying process with more checkpoints and decision makers than ever.
Compound that with the fact that they also have to navigate a sea of technologies all
designed to “help them in solving all this.” It’s no wonder Sales Leaders get overwhelmed
and ask: why can’t I just deal with one vendor that solves my sales stack?
Here at ToutApp, we’ve spent thousands of hours researching the art and science of
selling and have worked with our community of Sales Leaders to distill down the four
most important challenges that leaders are spending their budget, time and focus in
solving to win.
This strategic approach to addressing key challenges by using only a few solutions,
and age old best practices is being done by a new breed of Sales Leader—a leader that
combines the art of selling with cutting edge technology. These Sales Leaders are
following these practices to transform their team into a revenue generating machine.
Tawheed Kader (TK) is the Founder
and CEO of ToutApp. Prior to founding
ToutApp, TK worked at Bridgewater
Associates as a Technology Associate
and Plaxo as a Product Manager. TK has a
breadth of experience in sales, marketing,
engineering and entrepreneurship.
Every Sales Leader faces the same challenges, but few know how to diagnose and overcome their laundry list of challenges. With
this eBook, we set out on a mission to distill it all down to four top challenges. The information presented in this book is based on
hours of research we’ve conducted in order to build ToutApp and builds on the experience of Sales Leaders like our very own Frank
Swain, who took multiple companies from $0m to $35m+.
FIRST LET’S COVER SOME STATISTICS ON THE CURRENT STATE OF SALES:
• 33% of a Salesperson’s time is actually spent selling. - CSO Insights
• The average company spends $10K - $15K hiring an individual and only $2K a year in sales training. - The Bridge Group
• Only 57% of reps said they are equipped with strategies, tools and skills to exceed their numbers. - Harvard Business Review
• 67% of all Salespeople do not attain individual quota. - Altify
So, that’s the bad news. The bad news is that even with the excess of technology, enablement and sophistication, Sales is still not
winning. What’s the good news? The good news is you can build a revenue generating sales stack that supports your playbook.
1 Every Sales Leader wonders, why can’t every single rep perform like their top performer? Top performers
consistently outpace the rest of the team by an order of magnitude. The Sales Leader’s challenge is how to
identify what’s working for top performers, and implement it across the team.
What’s the single thing that you believe will make your team successful? Consistency. A well defined sales
process aided by Sales Enablement yields consistent messaging and processes to get to a successful
sale. Great Sales Leaders refer to it as “one smooth sales motion” and the key to achieving it is driving
consistency across your team.
Traditionally, Sales Leaders have tried to instill best practices and consistency through hours of sales
training in a sales kickoff. But, studies show that within 30 days of a training event, 79% of what people
have been taught is forgotten.
Today, Sales Leaders are embracing consistency using software that reinforces best practices, consistent
messaging and consistent actions at every stage of the sales process.
Investment #1 - Driving Consistent Messaging in the Sales Process
According to TeleSmart Communications, only 13% of customers believe a Salesperson can understand
their needs. To overcome this challenge, you need to match your product’s value to a customer’s pain
points. That’s where very crisp messaging comes in.
COMMON CASES WHERE YOU WANT TO DEFINE CONSISTENT MESSAGING INCLUDES:
• Messaging tying a customer’s pain to your product’s value proposition
• Clearly articulating the ROI your product delivers for your customer
• Accurately articulating how your product differs to competitors in the market
• Collaborating with Marketing to create clear collateral that will helps navigate negotiations through
procurement, security reviews and other gatekeepers.
In delivering a consistent message that resonates with a customer’s pain points and business needs, it
shows customers that your reps are actively listening to customers and working to solve pain points.
Field Sales forces and Inside Sales machines still have to follow up on critical meetings with well crafted
messaging over email, articulate value over the phone to drive a deal forward, and even embrace social
media to forge relationships casually.
In all of these interactions, having a clear strategy in messaging is consequential.
Investment #2 - Driving Consistent Actions in Your Playbook
The second investment in driving consistency revolves around standardizing the sales process across
the team. This means having your reps follow a consistent, repeatable and documented sales process of
delivering value and consistent messaging at every stage.
A CONSISTENT SALES PROCESS SOLIDIFIES THE FOLLOWING OUTCOMES:
• Qualified pipeline at the appropriate sales stages
• Accurate visibility into state of pipeline
• Improved visibility to enable accurate forecasting
You need a way to measure that reps are following the process and checking off the box of “I sent this
email at this stage,” before sending out the next communication. Being able to measure the process gives
Sales leaders visibility into:
• Where deals are in the pipeline
• Where reps are getting stuck
• Being able to predict how reps are performing in relation to their number
• Health of opportunities in pipeline
How to Beat the Challenge
Sales Leaders today utilize ToutApp’s platform to automatically recommend the best messaging that
alleviates customer pain, drive consistent actions with your playbook and aligns Sales and Marketing together.
“We’ve standardized the specific touches at various
stages of the sales cycle and as result we have a
much more predictable outcome. We know that a
prospect in a certain stage is going to benefit from
a subset of case studies that we send and track the
attribution to the case studies and ToutApp
analytics function allowed us to do just that.”
- Dan Miller-Smith,
Director of Sales at Procore
• Steady and consistent increase in win rates
from 14% about 12 months ago to 22% across
• Collapse of their sales cycle length—it used
to be three - four months and it’s been
compressing consistently down to 40-50 days
• 70% of Account Executives, that are attaining
quota, are hitting as much as 200-300% of
Pipeline is the leading indicator whether or not
your team is going to hit their number. Many
Sales Leaders struggle with having a solid view of
the health of their pipeline. We’re sure that you’re
familiar with these common pipeline questions:
. Does the team have enough qualified
. pipeline to hit their number?
. Does the team have enough new
. opportunities to add to the top of their
. Is there a well defined plan around how
pipeline is generated?
. Are reps able to manage pipeline as it
moves through the sales stages?
Every Sales Leader is struggling to find
answers to those common questions. Having
enough pipeline is the life-blood of your
business. You need to have it if you want to
close deals and meet your business goals.
That seems obvious, but pipeline creation and
coverage remains a top challenge for Sales
However, many Sales Leaders are beginning
to realize that there are two core areas to
invest in to conquer this challenge.
Investment #1 - Defining Responsibilities Around Pipeline Generation
If you want to overcome your pipeline challenge, the first thing that needs to be solidified is defining
who owns pipeline generation.
TAKE THE TIME TO STRATEGICALLY THINK ABOUT WHO SHOULD OWN PIPELINE
GENERATION AND WHY THEY SHOULD OWN IT:
• Are the individual reps responsible for building their own pipeline?
• Do you segment your Sales team between Account Executives and Sales Development
Representatives with the latter owning pipeline?
• Should Marketing be held accountable for pipeline?
These are all critical points to consider. The answers will make up your playbook for your business. You
need to take a stance on pipeline generation and hold either your reps, a Sales Development team or
Marketing accountable to its production.
Investment #2 - Defining Consistency for Pipeline Generation
When Sales Leaders are looking to define responsibilities around pipeline generation, the next step is to
define how to create consistency around it. There has to be consistency around messaging, in follow-up
and in actions—consistency in pipeline generation is no different.
If there’s no consistency around pipeline creation, how are reps expected to hit their number quarter
after quarter? With this realization, Sales Leaders are beginning to implement different strategies in
order to create consistency.
Account Based Sales and Marketing
According to ITSMA, 78% of executives are willing to respond to unsolicited outreach from companies,
if it contains ideas that are strategically relevant. Deploying both an Account Based strategy for Sales
and Marketing allows for multiple strategic sources of targeting and outreach that will fill the top of
Through these strategic approaches, your Sales and Marketing teams can tailor your solution and
content to individual accounts, thus hyper-personalizing experiences and turning accounts into
Multi-Touch Outbound Sales Campaign
For reps that need to generate pipeline, effective pipeline generation heavily depends on how well
equipped reps are to manage their pipeline. Reps need a scalable outreach communication workflow that
allows them to touch every opportunity, no matter the stage of the said opportunity. In short, reps need
to communicate with their opportunities across email, phone and social in order to generate pipeline and
move them through to the next stage in the process.
Sales Development Team
One movement among Sales organizations is segmentation between closing deals and prospecting
roles. Of the organizations implementing this strategy, their Sales Development team is responsible for
generating pipeline and booking meetings for their quota-carrying counterparts. Meaning, all outbound
communications is done through the Sales Development Representative (SDR) up until a lead is qualified
and turned into a working opportunity.
Automation Through Marketing
Marketing plays a huge role in generating Top of Funnel leads and nurturing them in becoming a qualified
lead. If tasked with generating pipeline, it’s not enough for Marketing to loosely define leads and throw
them over the fence to Sales.
How to Beat the Challenge
Sales Leaders today are heavily investing in tools that increases pipeline coverage in a scalable and
predictable way. ToutApp’s platform offers integrated Sales Campaigns which allows reps to run a well
defined and consistent multi-touch campaign so that prospecting for new deals (if your closers are
prospecting) or wondering if the fresh out of college SDR you’ve hired is pushing hard enough—is never an
afterthought. Further, Product Marketing can contribute and oversee the best messaging and see real-time
insights on what’s resonating.
3 Today, according to CSO Insights, companies will spend nearly $20K per year/rep to improve
productivity. And yet, rep productivity remains at an all-time low, with reps only spending 33% of their
time on actual selling.
Overburdened with non-quota attaining tasks such as data entry, submitting internal requests for
collateral, finding their own content, etc—reps are losing focus on their pipeline. According to Forbes
Insights, “71% of C-level executives know that sales productivity is, in fact, paramount to enabling a
company to grow.”
WHAT WE’RE SEEING IN THE MARKET TODAY ARE SALES LEADERS WHO ARE ACTIVELY
WORKING WITH THEIR REPS TO IMPROVE PRODUCTIVITY BY:
• Reducing the number of mandatory fields in the CRM to get a deal
• Implementing CPQ tools to streamline the quote-to-cash process
• Adopting effective sales tools that eliminates manual data entry
• Investing in Sales Operations to unburden reps from administrative tasks
Investment #1: Consolidating Tools
Ironically, we constantly hear about “tool fatigue” from Sales Leaders. With over 300 different sales tools
on the market, what started as a tool that helped reps has turned into an unmanageable toolkit that doesn’t
If this unmanageable toolkit is overwhelming reps—it’s a sure sign that you’re overspending on invaluable
tools. Instead of cobbling together eight different solutions for sales productivity, embrace consolidation and
focus on a few tools that align with solving rep productivity and your business needs.
Rather than spending on a productivity tool, a dialer, a tracking tool, etc.—purchase the vendor that offers a
full solution, not just bit and pieces. If reps are only spending a third of their time on selling activities, often
toggling between those eight different tools, that’s not an effective approach.
Investment #2: Automating the Process to Increase Capacity
Sales will never be automated, but smart Sales Leaders are embracing the notion that the menial aspects
of the sales process must be automated. Would you rather have your most expensive resource (the Sales
team) focus on closing deals or spending hours on data-entry?
If you don’t focus on automating low-value tasks, the friction that currently exists will continue to persist—
which doesn’t help rep productivity. You need to invest in a tool that automates tasks like updating your
CRM, creating tasks to send follow-up emails, setting up an email campaign with longer-cycle opportuni-
ties, etc. Through automation, it allows reps to focus on their warm opportunities while either eliminating
repetitive tasks or staying top of mind with longer-term prospects.
SIMPLY PUT, AUTOMATION IMPROVES A REP’S CAPACITY TO DO MORE SELLING AND AL-
LOWS THEM TO FOCUS ON:
• Having meaningful conversations with prospects to move deals forward
• Managing the number of active opportunities in their pipeline
• Shortening the sales cycle by having a laser focus on delivering value to prospects
• Driving higher close rates (while leveraging automation) and increasing the Average Selling Price
Focusing on sales capacity allows everyone to know how many opportunities need to be in the pipeline
and the number of opportunities that need to close for reps to hit their number.
Investment #3: Sales Enablement as a Discipline
The responsibility of Sales Enablement is to provide reps the
resources and skills they need to deliver your product’s value
proposition to match a customer’s pain points.
THE SALES ENABLEMENT DISCIPLINE CARRIES OUT
THE FOLLOWING RESPONSIBILITIES:
• Establishes a process that every rep can follow
• Ramps new reps faster
• Refreshes the skillset of seasoned reps that are looking to
grow and learn
• Plays a critical role in driving value to customers
As companies continue to scale, Sales Leaders will continue
to invest in Sales Enablement because it alleviates the sales
productivity challenges imposed on them. When reps are
equipped with the right content, the right talk track and know
how to handle customer objections—that drives an efficient
How to Beat the Challenge
The most effective Sales Leaders
rely on ToutApp as the one-go-to
platform that consolidates tools while
solving for friction at every stage of
the sales process. ToutApp focuses on
auto-logging to your CRM, providing
a dialer and gives reps real-time
insights into their communications—
literally putting minutes back in a rep’s
day, so they can focus on deals.
4 Lack of visibility into the sales process, pipeline and the
ability to hit your number is a constant source of anxiety for
Sales Leaders. Even with Salesforce dashboards, countless
forecasting tools, Sales Leaders are still relegating to an excel
spreadsheet to track deals as the quarter end approaches.
You may already be tracking a handful of metrics, but we’ve
condensed that list to just four core metrics that you should
track to get a clear view into your team’s performance.
Pipeline coverage gives you a clear view of what’s going to close and
what’s upcoming for the quarter. Without this metric, there would be no
visibility into where reps are in the process and/or if they are consistent
in following through in the sales process to meet their number.
FOR MANY SALES LEADERS, PIPELINE COVERAGE IS
FURTHER BROKEN DOWN INTO FOUR SUBSIDIARIES:
Tracking this metric gives
you insights on if your
reps are closing deals, but
more importantly it gives
you intel if reps are being
consistent in messaging
and accurately conveying
your company’s value
proposition to customers.
In the market, leading
companies hover around
a 20% close rate with a
5x pipeline that ensure
their projected close rate.
The number of opportunities
in the pipeline
Qualified opportunities where
value matches pain
The speed at which an opportunity
converts at each stage
The percentage of active opportunities
in period that convert to closed
Tracking deal size tells you how many opportunities you
need to meet your revenue goals. There is a finite number
of opportunities a rep can handle in a given period, knowing
deal size will help with planning rep capacity.
By looking through your company’s closed deals data, you
can find the average deal size which will help you target
your selling approach, messaging and content that will
increase the overall deal size over time.
Consistency Across Goal
According to Forbes Insights, 74% of the highest-performing
Salespeople focus on “consistency of execution” across
their sales process. This consistency of execution directly
relates to the number of reps hitting their quota quarter
after quarter, which increase your company’s Average
Selling Price, close rate and makes the sales process more
4 74%of the highest-
The time for cobbling together eight different point solutions is over. Our goal here is to
help Sales Leaders transform their team into a revenue generating machine. Through our
research, we’ve developed ToutApp’s Sales Success Platform to be a consolidated sales
success platform that addresses each of these key challenges.
TOUTAPP’S SALES SUCCESS PLATFORM HELPS YOU:
Increase Pipeline: Our integrated prospecting solution allows reps to send consistent
messaging, build account lists and call a prospect when they see real-time engagement
with their emails—all to build a more predictable pipeline for your business.
Drive Consistency: Rather than guessing what’s the right sales process to follow, our
platform enables you to deploy your playbook and drive consistent performance across
Forecast accurately: With more pipeline and consistency across the process, you’ll gain
visibility into every aspect of the sales process and forecast accurately. Thus turning your
sales team into a revenue generating machine.
Today, the average sales team shares 50+
templates across their team—making it
difficult to determine which template will
resonate most with the intended audience.
With Recommended Templates, it’s easier
than ever to deliver effective messaging and
value to customers.
THESE TEMPLATES ARE BASED OF
YOUR CRM FIELDS SUCH AS:
• Opportunity Stage
Instead of getting stuck on messaging, with
Recommended Templates that based on
your company’s CRM fields, reps can send
the right message at the right time.
Effective sales means having a repeatable process that reps can apply to every opportunity
in their pipeline. Sales Campaigns automates a rep’s workflow and follow-up process and
allows scale at reach. Here are a few uses cases:
1. While reps are working active opportunities, they can create a Sales Campaign that
will run in the background that will help them identify the warmest leads to follow-up
2. For a longer sales cycle, or if it’s not the right time to buy for a customer, reps can
create a Sales Campaign to maintain the relationship.
3. In high-velocity sales, reps have a higher number of opportunities, but managing that
velocity isn’t scalable. Reps can create a Sales Campaign to manage the flow.
4. For expansion sales, like cross-sells, reps can create a Sales Campaign that targets
different parts of the organization.
5. For a Field Sales reps, after an on-site, can create a follow-up campaign (start off with
an email) to remain in contact with the customer.
WhyYouNeedaSalesSuccessPlatform Integrated Dialer
Whether your reps are Inside or Field reps,
the sales process wouldn’t be complete
without both email and phone calls. While
a highly personalized email with relevant
content can be engaging, having a casual
conversation with the customer in real-time
is equally important.
Through Tout Phone, an integrated dialer
that allows reps to call a contact, use Local
Presence and record calls for reviewing
later—and the call activity auto-logs to your
Tools for Your Reps
Save time by creating
an email template that
corresponds with a specific
stage in the sales cycle.
Track opens, forwards,
replies, content engagement
and website link clicks,
so reps can follow-up
With each touch, reps can
create follow-up tasks right
within Gmail or Outlook.
RING THE GONG
Let your entire team
celebrate together when a
rep closes a deal.
AUTO-LOGGING TO CRM
Half the battle with Sales
is remembering to log
activities to your CRM,
instead rely on auto-logging.
Without leaving their inbox,
reps can select times they’re
available and insert them
Measure and coach your
team on what works and
A/B test for continuous
Prioritize pipeline and easily
follow-up with opportunities
with a call or email in a click
of a button.
ToutApp transforms your sales team into a revenue generating machine. The platform allows enterprise
sales teams to increase pipeline, drive consistency and forecast accurately. Founded in 2011, ToutApp
has more than 100,000 Salespeople using the platform, with over 500 enterprise customers including
SolarCity, Procore, Citrix, Apptio, Mixpanel and more.
For more information please visit www.toutapp.com
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