ARTICLE

THE FUTURE
OF SALES
Dave Boyce | Chief Strategy Officer
Chris Harrington | Chief Executive Officer
 THE
FUTURE
OF SALES

Dave Boyce Chris Harrington

Chief Strategy Officer at XANT Chief Executive Officer at XANT

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 “There’s no going back to the future and no new normal. This is a watershed moment. B2B sales
leaders must embrace change and plan for a very different buying and selling landscape.”1

Mary Shea, PhD. | Forrester

If you run a B2B business, ask yourself: Illustration:

Peter Slattery

“Does my sales operation look more like 1990s Oracle

or more like Crowdstrike, the fastest-growing SaaS
company to IPO last year?”

If you are like 1990s Oracle, you probably have:

• A large and well-paid field sales force

• Large average initial deal sizes (>$100K)
• 9-12 month sales cycles
• Lumpy bookings on a quarterly basis
• Poor bookings forecast accuracy “Outdated?!”
• Difficulty knowing what each rep is doing on any
given day / week The world has moved on.
If you are like 2020 Crowdstrike, you probably have: Modern B2B companies are maintaining growth rates
• A large remote sales team, complemented with field of 40% and higher (Crowdstrike was 107% in their IPO
sales quarter), and the modern engine room of growth is:
• Highly active marketing and demand generation • Demand generation
• Smaller average initial deal sizes (<$50K) • Inbound and outbound prospecting
• 3-6 month sales cycles • Remote sales
• High expansion rates • Customer success
• Smooth bookings growth, quarter to quarter Many companies have laid off or “retired” large portions
• Consistent bookings forecast accuracy of their field sales forces (monitor this here), in favor of
• Complete visibility into daily and weekly sales inside sales.
activity If you think the world will return to field selling after
the 2020 pandemic subsides, you will be waiting a long
time.

Sales is never going back.

Mary Shea, Forrester: “The Democratization of B2B Sales,” Aug 3, 2020

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Modern Selling • Afternoons
• Scheduled sales meetings
To understand the future of sales, let’s look at a modern
B2B seller’s daily life. • Scheduled team meetings
• Meeting Prep — Angela makes sure each
Angela wakes up where she lives--not necessarily co-
meeting has an agenda and an objective. Her
located with her company’s headquarters. She chooses
systems prompt her to send emails with this
where to live based on personal preference. She sets up
information in advance of her meetings to
shop in her home office and goes to work.
ensure expectations are aligned.
Angela logs into her systems, which track all her • Territory management — This time is used to
pursuits--top of funnel, mid-funnel, and bottom- plan how she will hit her number, research her
of-funnel. Angela has blocked out her day to focus accounts, add contacts to her lists, etc.
specifically on different parts of her business. Scheduled
• Follow-up — After each meeting, Angela’s
meetings take priority, but Angela concentrates these
systems prompt her to do the follow-up work:
in the afternoon where possible. Her team meetings
re-listen to the call, write the follow-up emails,
are in the afternoon too. Why? Her team has studied
assign the tasks, etc.
the data, and they know contact rates for prospecting
In order to break up each day and week, Angela
are 15% higher before noon.
schedules time for herself--she goes to the gym and she
• Mornings hikes in the hills near her house with her dog.
• Sales Development Rep (SDR) coordination
— At the beginning of each day, Angela speaks
“The AE-SDR relationship is the most
important partnership in modern sales. When
with her SDR, reviewing yesterday’s activity
it’s working right, they can finish each other’s
and prioritizing today. The SDR does most of sentences. Strategy is defined by the AE,
the prospecting for Angela and alerts her when tactics are programmed by the AE, and then
new appointments have been set with specific, the SDR does as much as possible before teeing
targeted customers. up the AE to step in and take charge. Does this
• Prospecting — The bulk of Angela’s mornings mean the AE doesn’t prospect? No. Does this
are dedicated to phone calls. She finds if she
mean the AE isn’t full-funnel? Definitely not.
What it does mean is that the team of AE-SDR
doesn’t spend specific time prospecting each
works seamlessly to provide as much value to
day, her funnel will empty out. And for some
the customer and as much leverage to the AE
of her accounts, Angela would rather make as possible.”
the approach vs. letting her SDR do it--this is
all planned in advance. Angela, her manager Lars Nilsson, Global VP Sales Development
and her SDR have all studied the data and they Snowflake
know the time before noon is best for calling,
reserving afternoons for meetings.

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Angela and her SDR rely on 4 main systems to help stay other systems that pull data from the CRM and
on top of their business: push updates to the CRM.

1. Sales Engagement Platform — Angela uses a Sales Angela’s scheduled meetings are not introductory
Engagement Platform (SEP) to manage all her top- meetings. Since her buyers are likely millennials
of-funnel and mid-funnel activity. She programs or younger, they’ve already read up on her solution.
her SEP to automatically enroll new leads into They’ve read the website, checked online reviews, read
pre-built plays--some that she will run, some that analysts’ opinions, and even pinged their network of
her SDR will run, and some that will get handed- peers for opinions on her solution.
off mid-stream. This makes prospecting seamless. Angela knows her buyer doesn’t need a generic
For scheduled meetings, Angela’s SEP prompts her introductory pitch--what they need is expert advice.
with pre-meeting tasks and post-meeting tasks, so They need someone who understands their situation
execution is always flawless. The SEP also watches and use cases and then helps make sense of the various
for updates or interactions and enrolls people or alternatives for solving issues.
accounts into plays when certain behaviors are
This is where Angela enters the picture--the modern
observed, like opening a marketing email or going 3
B2B seller. Call Angela a concierge, a consultant, an
months without an interaction. This helps Angela
advisor, a coach--call her whatever you want, but this
stay on top of mid-funnel and dormant accounts.
is the modern seller.
Angela’s manager can see all customer engagement
activities--as well as play utilization and success The modern seller more likely asks to see what’s
rates--because this data is logged automatically. on the buyer’s screen than shows their own screen.
The modern seller wants to understand first, then
2. Remote Meeting Software — Angela uses a video
recommend. The modern seller knows they are a
conferencing service to deliver the meeting, manage
“tenant at will” in the relationship, and they could be
a chat window during the meeting, and capture
kicked out at the first sign of not adding value. So Angela
a transcript of the call for analysis afterwards.
adds value. She knows her stuff. She develops empathy
Angela’s manager depends on this call analysis to
and understanding for her customer’s situation. If
identify sections of calls to listen to, as well as to
there is not a fit, she moves on.
identify coaching moments.
The modern seller is:
3. Content Management — Since Angela knows she
has to add value in every interaction, she depends • Fast
on having the best content at her fingertips--ready • Always online
to refer to, display, and share. Content management • Customer-centric
is integrated seamlessly into the SEP. • Content-rich
• Technology enabled
4. CRM — This is the foundation and the system of
record. This is where Angela’s territory is defined, This is never going back to the old way. This is a
and this is where all notes, updates, and status durable shift for two permanent reasons:
changes are logged. It’s also how she gets paid,
1. Millennials are now in charge of buying
so she wants it up to date. She does not, however,
spend a lot of time in CRM--mostly she works in 2. Remote buying is better for everyone

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Digital Natives with a digital native requires showing up, adding value,
collaborating, and earning trust.
Millennials now make up 50% of the workforce.
Millennials, more than ever, are in positions of power So the modern seller becomes less of a merchant and
both on the selling side, and on the buying side. They more of a concierge, a consultant, or a coach.
are digital natives, and as such they lean toward more “Help me understand what you are doing today, and
technology, not less. The first place digital natives go what about that is not working for you.”
for answers is online, and they may not even look for a
keyboard--they may just ask Siri. Digital natives prefer “Yes there is a lot of information out there--let me
collaboration, and they are comfortable collaborating help you make sense of it.”
online. Once they feel they know enough about a “Depending on your specific need, you may want
product category to begin asking questions, they hit up to consider a product from my competitor, or my
their peers. Millennials are quick to text or DM (direct product may be best. I’m happy to help you make
message) a friend to see what they know about fill-in- that assessment.”
the-blank.
“Buyers don’t care how your internal
With these proclivities in mind, it’s no surprise digital organization is structured or what type
natives are not interested in a protracted information of seller is assigned to their account. They
exchange with a salesperson. And they are certainly expect every interaction to bring them
not interested in spending social time with a corporate value, relevancy, and continuity.”3
salesperson at a ball game or a golf course. Digital
natives would rather find the information they need on Mary Shea, PhD. | Forrester
the Internet. Modern manufacturers and vendors have
“In an attention-competitive environment
put more and more product and how-to information
memory decay is your enemy. You need new
online. And where the vendors themselves leave off,
ways to connect emotionally, embed precise
review sites, how-to sites, and the general public fill in
memories, and motivate action in your
information gaps, including reviews, suggestions, and
favor in a selling environment where the
guides.
buyer is in complete control of when, where
It’s been estimated a modern B2B buyer can complete and how they give attention. At the same
70-80% of her buying journey without ever talking to a time, they are overwhelmed and confused
salesperson. by all of their options and need your help.”
None of this means a younger, faster, more digital Tim Riesterer, Chief Strategy Officer
buyer is less empathetic, relationship based, or Corporate Visions
interested in building trust--quite the opposite.
More than any previous generation, millennials (and (For more on this topic, see The Future of Buying)
younger) care about ethics, trust, responsibility. And
they are comfortable doing business with or without a
personal relationship. But to build a true relationship

Mary Shea et. al., The Democratization of B2B Sales, Based on Forrester’s
2 3
Mary Shea, Forrester Blog
Q1 2017 International B2B Marketing Panel Online Survey

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Remote Selling • Examine all sales personnel — keep the ones who
are producing
Gone are the days of the onsite sales meeting. Remote
• Examine all sales processes — keep the ones that
video conferences have all but taken over corporate
are:
life, and every selling interaction can and will happen
remotely from this point forward. • Fast
• Always-online
Screen sharing obviates the need to present materials
in person. Multi-participant video conferencing • Customer-centric
obviates the need to assemble a large group in person. • Content-rich
Call recordings, auto-transcriptions, call summaries • Technology-enabled
and task capture--all make online meetings faster,
• Examine demand generation — Look specifically
more convenient, and in many cases more effective.
at how an inquiry turns into a lead, then an
The salesperson may still want to be in person to better
opportunity, then a deal. How much volume does
read body language and group dynamics. But the buyer
this demand generation engine produce? Is it fully
does not want this, and the technology facilitates a
technology-enabled? Can it feed your entire sales
reasonable alternative, so our new reality is largely
team?
remote.
“A modern sales process depends on tight
“Because you are no longer in the room with
coordination all the way to the top of the
your buyers, you need to find ways to be
funnel. Marketing focuses almost all their
more unique, memorable and convincing.
energy on specific demand generation
You need better stories and fresh skills to
feeding qualified leads into the funnel (you
deliver conversations that win in both the
can’t brand your way to greatness). And
digital self-serve dialogue and the virtual
sales pays acute attention to top-of-funnel
sales-led experience.”
activity, taking responsibility early and
Tim Riesterer, Chief Strategy Officer often to engage with leads as soon as they
Corporate Visions show interest.”

Richard Sgro | Modern Sales Pros

Building Your Sales Future
After this introspection, how much of your business
Let’s return to our earlier question: does your sales looks modern? Is it enough to reach your growth
team look more like 1990s Oracle or 2020 Crowdstrike? objectives? If not, now is the time to start building in
(Hint: Crowdstrike is configured for the future.) place of anything you may have eliminated.
If you don’t like the answer, now is the time to change. Consider the following methodology for this
Under the cover of COVID, we recommend the following: introspection / reinvention:

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 you keep them fed with demand generation? Will your
target markets support expansion? Theoretically,
the only limit to growing the modern portion of your
go-to-market motion is your ability to cost effectively
generate leads to keep that team fed. Could you expand
that team by 20%? 30%? 50%? Do it.
“Modern demand generation techniques can
increase the flow of qualified leads by up to
100% if you know how to implement and have
the patience to tune the engine. Between
intent detection / attribution, website tracking,
and marketing automation--both inbound and
outbound--we’ve seen many clients completely
scrap prior notions of how much demand is
available to harvest digitally. The marriage of
modern demand generation and modern sales
Step 1: Evaluate engagement is a match made for this moment
Divide your go-to-market motion into two halves--one in time.”
that is modern (follows the principles of modern sales
Steve Gustafson, COO | Search Discovery Inc.
outlined above), and one that is legacy.

Step 3: Extend
Step 2: Expand
The next step is to look at your legacy territories and
By how much could you expand the modern portions
evaluate how much of those historically “field-based”
of your business? Could you hire more reps? Could
territories could be effectively served by exactly the

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same modern processes as have historically served So how do we reinvent and retool in this segment to
other segments. If there were ever a time to re-evaluate continue taking advantage of your enterprise team’s
your go-to-market motions, it is now. And if you have unique skills?
in-house, modern processes that could serve other
This reinvention will fall into three categories: Skills,
segments, again: do it.
Processes, Tools.

1. Skills

There is no getting around the evolution of the B2B

buyer. Her preferences have evolved as outlined above,
and we must meet her where she is. Therefore, we
must be:

• Fast
• Always-online
• Customer-centric
• Content-rich
• Technology-enabled

To the extent your enterprise team can use skills

training here, do it:

• Training on the millennial mindset

Step 4: Re-Invent
You are now left with the segment of your business • Training on the speed of millennial communication
that is the “most legacy” of all. This segment likely • Business writing skills work
contains your most expensive and most productive • Training on the details of your product, your
field sellers--let’s call them your “Enterprise Team.” competitors’ products, use case fits, case studies,
They’ve historically landed your largest deals. They value calculations—if your team needs to be
take care of your most important customers. Their art content-rich, let’s get them the content!
and magic lies in their ability to work face-to-face with
2. Processes
customers, on-site, tackling enterprise-size problems
and opportunities. Since enterprise reps will not be Examine all your processes and make every single
welcome onsite at their customers for the foreseeable check and balance fight for its existence. Millennial
future, we must reinvent. buyers are not patient, and the speed of modern selling
doesn’t want to wait for approvals or sign-offs. If you
Let’s acknowledge this segment cannot and should not
can speed up your processes by eliminating steps,
go away. The reason you didn’t roll existing processes
automating approvals, streamlining pricing, etc.-- do it.
over this segment is because you didn’t think it would
work. The reason you didn’t fire these enterprise
reps is because they are experienced and productive.

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Here are some examples: • Pre-Call Preparation — Enterprise reps
can benefit from a checklist of what to do
• Can you record and transcribe calls so your reps
before a call: Templated emails / agendas for
don’t have to type up notes?
the customer. Standardized call prep docs.
• Can you use a quote-to-cash process that simplifies Served-up research on the account. SDR
approvals? (Or alternatively, can you kill your call recordings to review. SEPs have been
quote-to-cash process because it’s created too configured to facilitate all of this.
much overhead?)
• Buying Committee Identification — In almost
• Can you automatically log calls, emails, meetings no case do we start out on an opportunity with
into CRM to save reps time? all the relevant actors identified. The typical
• Can you document processes and handoffs so way an enterprise rep works to identify
collaborators (sales engineers, management, additional approvers, influencers, and buying
products specialists) know exactly where to find committee members is by walking the halls,
things and what to expect? having informal conversations over lunch,
and asking tons and tons of questions. Much
Even though “enterprise” is the least automatable of this can be replicated via remote and
segment of your business, you do not want every deal digital communication, but SEPs can also
to be a special snowflake that requires customized be helpful. Some SEPs can literally tell you
process and attention. Look for every opportunity to who else matters to a buying decision at that
define, document, and template processes. And that company, based on collective intelligence.
leads to the third category: Some can tell you which roles are still
3. Tools missing on your buying committee and guide
you to find them. But even if you don’t have a
Much of what you reinvent in 1) skills and 2) processes
prescriptive SEP, you can still enroll multiple
will be facilitated by tools--tools that need to be
people into plays that “warm up” influencers
implemented, configured, trained on, and adopted. We
and approvers and ensure you have each
mentioned the modern sales stack earlier, and although
member of the buying committee actively
the motions for your enterprise team may be different
engaged.
from the other parts of your business, the tools remain
the same: • Post-call Follow-Up — Once you hang up a
call, much of the work starts. SEPs can be
1. Sales Engagement Platform — SEPs got their
used to help you keep track of and manage
start with sales development teams, and they
that work. What notes get sent to whom?
have extended to inside sales teams and customer
What recordings? What to-dos get logged
success teams. But innovative managers have
and distributed? What follow-up emails get
also configured SEPs to facilitate enterprise sales
sent to the customer?
motions for their enterprise sellers who are now
working from home. Some cutting-edge uses for 2. Remote Meeting Software — This is the most
SEPs in an enterprise motion include: obvious category of software for erstwhile field

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 enterprise teams. We are all remote sellers now. generated emails, but also tracks customer
access to that content.
• Make sure your teams are using video tools
and not just resorting to cell phones. • Ensure your SEP triggers are set to fire off
additional communication when a prospect
• Train reps on how to encourage prospects
accesses a piece of content, a proposal, or
to engage over video and turn cameras on.
even a straight-text email.
This allows enterprise reps to build more
personal relationships and use their powers 4. CRM
of perception to read body language.
• CRM is the backbone of everything, and
• Winning by Design has great tips for how to historically it has been the only way to
manage remote meetings and get even more monitor the activities and progress of your
out of a remote meeting than an in-person enterprise team.
meeting. Top tips include using the chat
DO NOT SACRIFICE THIS
window strategically, using the white board,
and assigning roles on your side of the call. • Everything from your SEP, your remote
meeting software, and your content
• We’ve incorporated call recording software
management systems should write back to
into this category--whether you are
your CRM.
recording using native or third-party tools.
Call recordings, transcriptions, and analysis • This is how you run reports, combine data
can be very useful: from across your enterprise, and stay on top
of enterprise selling activities.
• Saves time for reps
“It’s not enough for systems to be siloed and
• Allows reps to review calls prior to passive in the era of the empowered buyer. A
engaging in subsequent calls—good for seller of the future is able to lean on a blended
strategic deal management tech stack to be prescient, to predict what the
customer will need, to personalize the buying
• Great for coaching
interaction, to surprise and delight. If you can
3. Content Management perfect selling interactions with automation,
ML, and AI empowered data, you will stand out.
• Since we are moving quickly, we do not want Standing out gives you a seat at the table. How
to create custom content for every deal--this you sell sets the tone for your CSM fulfillment
is where content management comes in. models and ultimately the perception of what
the customer experience will actually be like
• The best sales content management systems
behind the veil.”
curate current and relevant content and make
it easily accessible to reps. Justin Michael | Sales Futurist

• Be sure your content management system

not only allows seamless attachments to SEP-

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In Summary “The key role in any such change is middle
management. This is who will drive the move
The question is not when will sales go back to “normal.” from a ‘manage by activities’ to a ‘coach on
Sales is Never Going Back. The question is, how quickly outcomes’ approach.”
can you modernize so you can embrace the future of
sales and come out of COVID ready to take on the new, Jacco van der Kooij, co-CEO | Winning by Design
fast, always-online, customer-centric, content-rich, Here’s to your success transforming and re-tooling to
and technology-enabled world of modern buying and take the future head on. If you adopt Forrester’s current
selling: watchword of “Bold at Work,” you will succeed! If you
• In place of field sales, remote sales. come out of 2020 and still have a sales organization
• In place of ad hoc, technology-enabled processes. that looks like 1990s Oracle, you are 100% ready to take
• In place of “come one, come all,” targeting. on 1990s buyers, if you can find them. But if you come
• In place of manual, automated. out of 2020 ready to outpace your competition, meet
buyers where they live, and leverage all the tools and
• In place of travel, videoconferencing.
techniques of modern selling, look out world!
• In place of everyone for themselves, a Sales
Engagement Platform Rock on,
• In place of “hope they’re good at what they do,” sales
Dave Boyce
call recording and analysis
Chris Harrington
• In place of “custom presentations,” content
management
• In place of presentations at all, discovery sessions

Many advisory organizations know how to help you get

from here to there. Some of our favorites are:

• Search Discovery, Inc.

• Vertical Relevance
• Winning by Design
• Boston Consulting Group
• Justin Michael Consulting Resources
• Kraig Kleeman • XANT Playbooks
• Flip the Script • XANT: Sales is Never Going Back
• Winning by Design
• Sirius Decisions • Research
• Webinar on Remote Selling
Now is the time to retool your sales organization for • Inc.: The (Millennial) Workplace of the Future is Almost Here
the future. As you architect your sales model of the • Mary Shea et. al., The Democratization of B2B Sales, Based on
Forrester’s Q1 2017 International B2B Marketing Panel Online Survey
future, do not forget where the real work gets done. • XANT: The Future of Buying

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