B2B Sales Strategy: Winning Plays for Big Contracts

 Score Your Largest B2B Sales Prospects with Seven Elements

[Instructor] Picture this: you've uncovered a very large new prospect
opportunity. If closed, it would be worth more than five times your
average contract size. You may feel optimistic and uncertain at the
same time. You're also unclear about how to get started because you
know that really big prospects require higher-level plays. Thankfully,
you have an experienced sales manager who advises you to
assemble the opportunity team to score the prospect. Scoring is used
to compare and prioritize big prospects. It lets you know if the
opportunity has a high likelihood of success and ensures that the
team applies critical thought to each of the seven scoring elements.
Large opportunities are complex and messy, requiring the entire
opportunity team to think and act strategically over time. Gaps should
be identified and discussed upfront. The scoring process unites and
energizes the team to focus on the opportunity ahead. Download the
opportunity scoring worksheet, available in the exercise files, to follow
along.
The first scoring element is assessing the estimated financial value of
the opportunity. Is it significant and worthy of the selling team's time and
effort? The team scored their prospect with a five rating, meaning that
the estimated financial value is at the highest end of the scale. The
second element is strategic value. In other words, does the opportunity
represent strategic value for your company? An example of strategic
value is a prospect with a marquee name in a recognized industry, which
would attract other prospects. A productive method for opportunity
teams to score each element is through the discuss, debate, decide
model. Using this approach, the teams scored the strategic value of their
big prospect as a five.
The third element is fit. The opportunity team discusses whether the
prospect is a good match for your products and services. Fit is similar to
the qualification stage of your regular sales process but may not be as
straightforward for whale-size prospects. For example, complex
opportunities often fall outside normal deal timelines. The team scored
the opportunity as a four for fit, as part of the solution would involve
implementation in a new geography for your company.
The fourth scoring element is access. Does the selling team have
access to the buying committee, including key decision-makers,
executive sponsors, and stakeholders? In other words, can the selling
team secure meetings with these people? After much discussion and
debate, the selling team decided to score this element as a three on a
scale of one to five. They have access to some key people, but not all.
The fifth element is complexity. Complexity factors include the number of
people involved in the sales process on both the seller's and prospect's
sides, anticipated length of the sales process, number and intensity of
competitors, and perceived risk from the prospect in making a change.
The higher the complexity, the higher the rating. Complex opportunities
benefit from focused strategy work over a long period. The team rated
complexity as a four.
The sixth element is prospect commitment. The team must wrestle with
whether the prospect is committed to solving their problem and following
through on the buyer's journey all the way to closure. In this case, the
prospect has stated that they are committed to solving their problem;
therefore, the selling team scored this element as a four.
The seventh and final element is opportunity team commitment. The
team must honestly assess their long-term dedication to focusing on all
plays required to develop and close this extremely complex deal. The
team rated their commitment as a five. The score was tallied, and the
opportunity will now proceed with the next set of strategic plays to
advance their large prospect.
I highly recommend using the scoring worksheet for all your top
prospects. It's a tool I've developed and refined for my clients, leading to
millions of dollars in revenue for them. Set a time now to bring together
the opportunity team to score your largest prospect. If you're not familiar
with who should be on your opportunity team, I'll cover that later in the
course.
2. Create a Powerful Connection with Your B2B Sales Prospects

 [Instructor] Most senior salespeople agree that applying insights

based on effective research leads to more productive prospect
conversations. However, my experience shows that salespeople
often view research as an academic exercise, causing it to drop to
the bottom of their to-do list. We're going to dive into the concrete
 benefits of applying account insights and how and why this
approach works.
Assume you are an experienced account manager focused on the
financial services industry preparing for an executive review with your
largest account. The high-level planning meeting will include several key
stakeholders that you have yet to meet. Although the financial services
customer is satisfied with your services, there's a pesky competitor trying
to make inroads.
You start by gathering the full account team to discuss what they need to
know and how to apply those learnings throughout the customer
meeting. The account team decides they need a current view of the
company in addition to a deeper understanding of the department they
work with. They want to avoid any customer frustration by asking basic
questions that could have easily been answered through proper
preparation. The account team believes that sharing their insights and
ideas during discussions will differentiate them from their competitor.
Follow along by downloading the Applying Account Insights worksheets
from the exercise files. At the company level, the account team intends
to learn about the organization's top priorities and consider how their
services may positively impact those priorities. Key stakeholders will be
very interested in ideas that can help move their top priorities forward.
You and your team also want to uncover alignment points between your
company and your customer's company. Those areas of commonality
can lead to great connections with meeting participants. For example,
best practice ideas can be shared, which leads to new ways of
collaborating.
At the departmental level, the account team plans on learning more
about projects and initiatives—where most departmental resources are
focused and how you can help. Your company may have experience
that can be shared based on working with similar financial services
customers. The team can address problems they may be able to solve
and issues that your customer hasn't considered. This type of discussion
adds value for your customer and can lead to additional projects for your
company.
Once research has been completed at both company and departmental
levels, it's time to learn more about meeting participants, especially key
stakeholders that the team has yet to meet. The account team decides
to compile a background and common connections brief for each
meeting attendee and talks with their day-to-day contact about each
participant's style and disposition. They will apply this knowledge by
matching members of the account team with customer contacts where
there is mutual interest.
The final step for the account team is to incorporate what they've learned
into a meaningful agenda that includes plenty of discussion points. A
successful executive review and planning session will reinforce your
company's positive impact on its largest customer while setting the stage
for future expansion opportunities.
Creating a powerful connection based on applying insights also means
neutralizing your competitor; they simply won't be able to keep up.
3. Analyze Your Sales Opportunity: Strategic Actions
Now picture yourself as the VP of Sales for a global consumer
goods company. Your team of tenured salespeople sells products
to large companies that, in turn, sell them to consumers. One of
your account executives has identified an extremely large
prospect; however, the sales process will be lengthy and complex
since this prospect has a longstanding relationship with a
formidable competitor. Who would you pull onto the opportunity
team?
The opportunity team should include individuals who can move the
opportunity forward; core team members and resources will vary for
each prospect. In this case, since the sales manager knows the prospect
well, they should be included along with an expert from product
marketing who is familiar with the competitor and lastly, the future
account manager who will lead once the prospect converts.
Today, your team tackles the opportunity analysis snapshot—an
exercise designed to provide a strong picture of the current state along
with a starting point for building strategy and goals. This exercise helps
teams think strategically about opportunities while generating immediate
action steps.
Most importantly, analysis offers key insights into prospects'
perspectives. Here's how it works: download the opportunity analysis
snapshot worksheet from the exercise files.
Your team begins by putting themselves in their prospect’s shoes,
considering how they view your company’s strengths and weaknesses—
this outside-in thinking is powerful. After capturing these viewpoints, your
team develops action items aimed at building on strengths while
addressing weaknesses.
For example, one weakness identified was distribution in a remote area
where the prospect operates; your team brainstormed ways to minimize
this weakness by partnering with a distributor servicing that remote area.
Next, you encourage your team to continue viewing things from their
prospect’s perspective by identifying possible threats—such as how
making supplier changes could be perceived as risky.
This realization leads to discussions about mitigating real or perceived
risks associated with change; one practical idea was introducing their
prospect to a customer who had made a similar change while including
future account managers in key meetings to share information about
how transition and implementation would work.
The final consideration involves exploring what opportunities prospects
might see in working with your company—this yields several new
engagement ideas; for instance, inviting their executive sponsor to
participate in an annual gathering where key customers share ideas
could be beneficial.
Once confident they’ve thoroughly analyzed strengths, weaknesses,
opportunities, and threats from their prospect's perspective, instruct
them to flip their viewpoint—analyzing current opportunities using this
same model.
As VP of Sales, you’re proud of your opportunity team's work; by
session's end they could see both their perspective and that of their
prospects clearly while agreeing on action items aimed at building
strengths, minimizing weaknesses, capitalizing on opportunities, and
neutralizing threats.

4. Create Your Big Complex Sales Prospect Strategy and Goals

 [Instructor] A play often overlooked by selling teams is taking time

charting strategies and goals for big complex opportunities—a
mistake indeed! A well-crafted strategy keeps teams focused on
 what's most important; it serves as "True North," guiding them
through complex waters during large sales processes.
Luke, an account executive at a large regional insurance company
understands that charting an opportunity strategy ensures that everyone
is aligned on objectives; he gathers his selling team for a win room
session focused on their national automotive prospect.
The team has already scored this opportunity, gathered insights, and
completed an opportunity analysis snapshot prior to this meeting; Luke
kicks off by defining an opportunity strategy—clarifying selling priorities
while helping set goals.
This strategy is internal but incorporates learnings from previous work—
download charting account strategy worksheets from exercise files. Luke
explains that strategy statements might begin with words such as
introduce, expand, multiply or replicate; they should be simple enough
for everyone on board while answering: what are we aiming to do?
Here's an initial draft developed by Luke's team: “Our strategy is to
expand our services into our growing marketing division by capitalizing
on our long-standing relationships within research.”
Great start! But wait—the strategy needs testing; Luke encourages his
team members challenge themselves with these questions:
 Is it consistent with our prospects’ priorities based on what we’ve
learned?
 Does it build upon our strengths while capitalizing on identified
opportunities?
 Does it address any perceived risks?
 Is it action-oriented?
 How might competitors respond?
 Is it clear enough for all members?
Once satisfied with their strategy’s effectiveness it’s time for goal
setting—focusing on critical elements that will propel them toward
achieving outlined strategies.
The team determines several short-term and long-term goals:
 1. Meet with key contacts in research division by month’s end—learn
about marketing division’s priorities.
2. Talk with executive sponsor regarding introductions needed for
senior director within marketing division by quarter’s end.
3. Secure meetings with senior level director before year-end.
By conclusion of win room session focused on charting
strategies/goals—Luke’s team gained clarity regarding direction/action
items significantly advancing big prospects!
 Explore Relationship Mapping in Your B2B Sales Strategy
Instructor] My clients frequently ask about defining complex
opportunities—a complex sale revolves around intricate issues
your prospect is committed towards solving; one primary
characteristic includes numerous stakeholders involved—
experts/users/decision-makers/executive sponsors creating
challenges for account teams managing relationships while
maintaining progress.
Picture yourself as an account manager within executive staffing firm
servicing healthcare industry—your responsibility entails
retaining/growing top three accounts within region; early on you learned
about power behind relationship mapping—it offers comprehensive
views regarding position relative each key relationship—highlighting
gaps/strongholds!
You gather your account team—including sales manager/customer
success associate—to develop mapping strategies; now’s perfect
moment grab relationship mapping exercise file!
Your team decides together map existing relationships alongside those
needed largest healthcare customer; then analyzes each relationship
developing objectives tailored towards individual contacts—for instance
starting off executive sponsor Brad—the chief medical officer—first
discussing his role relative buying committee—decision
maker/validator/stakeholder?
Account team remains unsure—a positive outcome revealing need seek
answers—next element focuses Brad’s influence regards staffing
services—is it high/medium/low?
In this case—account team recognizes Brad possesses high influence—
they’ve taken note his opinions carry weight! Following part involved
gauging position relative offered services—is Brad strong
promoter/neutral/threat?
Given past interactions—team feels confident labeling him strong
promoter! After examining mapping factors regarding Brad—their
objectives develop moving forward centered around establishing
connection between Brad & chief revenue officer—they’d share many
commonalities!
Mapping relationship reveals clear understanding best pathways
forward; outlining critical relationships assists account teams prioritize
time spent developing connections!
 Develop B2B Sales Win Themes for Decision-Maker Receptivity

I can't recall any clients closing exceptionally large contracts without

engaging true decision-makers—one biggest challenges today
revolves around accessing high-level executives or sponsors—who
are increasingly difficult due competing priorities consuming valuable
time!
One essential play within big deal contract playbook entails
developing/deploying win themes; these represent intersection points
connecting decision-maker’s priorities alongside strengths offered by
your company positively impacting those goals!
Win themes form sweet spots aligning receptivity between you &
executive sponsor allowing conversations focus highest value areas
rather than mere pain points/needs associated solutions!
I regularly guide clients preparing presentations; recently worked
alongside regional sales manager engineering firm prepping finalist
presentation aimed at executive audience engaging full opportunity
teams developing clear win themes resonating attendees!
Team recognizes previous presentations indicate differentiated
approach neutralizes competitors! I remind them begin understanding
top-level priorities executives emphasizing importance why each
matters!
Research proves beneficial—but truly understanding requires asking
stakeholder (internal champion) where executives allocate
time/resources currently!
Team discovers retaining tenured architects stands foremost priority
senior decision-maker—they’ve lost several top architects competing
firms requiring experience/expertise support growth!
Equipped specifics—I guide teams assessing strengths capable
positively impacting priorities! Final win theme formula portion entails
adding evidence supporting claims engineering firm advances executive
sponsor’s goals!
I suggest including stories/testimonials similar clients experiencing same
priorities illustrating positive impacts! During finalist presentations—their
engagement signals success—asking questions seeking details—and
even requesting further introductions!
Ultimately—their contract secured ensuring ongoing access executive
sponsor trust cultivated through alignment relentless focus priorities!
7. Engage Your Executive Sponsor To Win Large B2B Deals
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 [Instructor] Once targeting executive sponsor services—it’s crucial
establish strategic engagement over time! Too often I observe
selling teams laboring months securing meetings high-level
decision-makers/executive sponsors only see engagement cease
once concluded leaving feeling exposed without support!
This play centers around smart ways keeping doors open! To gain
insight—we’ll interview Mia—the Chief Revenue Officer global
technology company; she’ll share her thoughts regarding engaging top-
level decision-makers effectively!
Mia—we appreciate your time helping us understand engaging decision-
makers like yourself! We know executives vigilantly guard time—what
prompts acceptance meetings?
 [Mia] I only accept meetings senior salesperson or executive
company when I’m confident they’re informed about me/my
business! I need assurance learning something new during
conversation—for instance discovering something hadn’t
previously considered moving top priority forward! Conversely—if
solely focused products/services—I won’t meet again!
 [Instructor] Makes perfect sense! What should salesperson aspire
achieving during meeting keep door open future engagement?
  [Mia] Absolutely—they must demonstrate active listening; only
afterward should offer something valuable like
introductions/resources/data inaccessible otherwise! I recently met
executive salesperson who understood core business problem
sharing relevant study narrowing options—I’m now open dialogue
with that executive!
 [Instructor] Mia—are there windows opportunities executives
should recognize cultivating collaboration?
 [Mia] Certainly—I always allocate time kicking off essential projects
involving key personnel! Briefings updates project progress
mattering greatly—I want clarity roadblocks if any exist enabling
me remove obstacles!
Additionally—I relish opportunities recognizing my teams’ successes
during project milestones! Finally—I find engaging high-level planning
around top priorities incredibly valuable—for instance one long-term
supplier includes me multi-year strategy sessions aligning mapped
projects initiatives!
This strategic supplier enjoys open door policy—they understand me
appropriately engage throughout year!
 [Instructor] As demonstrated through Mia’s interview—executives
facilitate progress removing roadblocks/providing resources
aligning initiatives fostering collaboration! They inherently focus
long-term hence respond favorably cultivating engagement
strategies over time!
Mia provided unique suggestions which culminate forming play
executive engagement challenge conducting interviews one executive
sponsors learning best collaboration methods over time!
8. Sales Proposals: Avoid Missteps And Create Strong Bid
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 [Narrator] When dealing large B2B complex opportunity proposals
numerous forms merit consideration including finalist
presentations/responses RFPs/request proposals standard but
likely more detailed proposals! Play seeks improve proposal
approaches yielding more contracts!
Imagine yourself role account executive seeking enhance proposal-to-
contract close ratios; recently several proposals stalled resulting
disheartening experiences—they decided address topic next sales
meeting exploring common proposal missteps/strategies avoid future
pitfalls!
Team concludes most prevalent misstep revolves around failing engage
prospects during proposal development phase—they often create
proposals isolation presenting final products instead collaborative efforts!
Better approach involves working sessions refining service
scope/options desired while allowing sellers clarify problems seeking
resolution impacts hoped achieved!
Working sessions focus content refinement—not pricing! Additionally—if
key elements were missed during qualification stage—they can gather
insights within these working sessions—once every detail agreed
upon—it becomes straightforward finalizing proposals resulting buy-
in/acceptance from prospects!
Second misstep discussed involved generating proposals centered
around you rather than focused prospects; several members admitted
using generic templates highlighting their own offerings rather than
articulating prospective issues/opportunities!
Some included jargon/acronyms unknown leading glazed-over
expressions amongst audience unable connect solutions proposed
issues faced!
Team concluded flipping proposals towards prospect-first perspective
beneficial beginning descriptions detailing issues/opportunities
concluding summary impacts expected via recommended solutions!
Including three options empowers prospects providing choice while
incorporating proof like client testimonials evidencing solution
effectiveness adds value!
Moreover—all statements regarding solutions should articulate benefits
prospects derive while highlights regarding companies remain pertinent
most important aspects addressed directly connected them!
Strongest proposals maintain 100% focus prospects throughout resulting
improved understanding value being offered translating into agreements
moving forward!
Final misstep involves sending proposals without scheduling review
meeting however prospects often request receiving them without
discussions occurring!
Team agrees sending proposals without meetings risks stalls—a tale
illustrating Sacha continually sending proposals without review meetings
illustrates this point well!
Coaching Sacha—reminded her track record stalls stemming from
approach—we agreed changing methods moving forward! Next time her
prospective client requested proposal she emphasized reviewing
together greatly benefiting parties involved!
Sacha informed prospect many aspects within proposal necessitate
discussion/input refining few elements capturing notes spot answering
questions ensuring next steps defined during proposal meeting while
engaging decision-maker through contacts established earlier remains
prudent necessity!
Sales teams energized discussion committed applying remedies
proposals going forward resulting improved proposal-to-contract ratios
dramatically enhanced overall effectiveness seen across board!
9. Sales Deal Closure: How To Sustain Prospect Momentum
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 [Instructor] Within realm 5x deals contract worth at least five times
average sizes—you’ll require Big Deal Playbook assisting maintain
momentum navigating lengthy often messy sales processes! Five
themes run through playbook viewed secret sauce
developing/closing 5x deals!
It begins leadership—the opportunity requires strong leaders steering
group towards strategies/goals achievement facilitating progress
throughout process! This facilitator might be an account executive/sales
manager/company leader—but must possess clarity regarding elements
big deal playbook balancing communication skills paired
strategic/tactical mindsets ensuring right people deployed effectively
throughout stages involved!
Team member commitment forms bedrock long complex processes
once opportunities scored commitment entails seeing through active
participation win rooms tackling action items focusing outcomes
sustaining momentum maintaining connections established!
Team members need proactively communicate progress understanding
roles shifting responsibilities may differ job titles; technical resource
could serve critical thinker during win rooms while customer success
manager offers constructive skepticism throughout processes ensuring
alignment perspectives fostered all parties involved leading successful
outcomes achieved consistently!
Winning teams maintain prospect/customer-first perspectives prioritizing
buying groups’ journeys filled ambiguity/stressors align selling teams
keeping front centers every step along way!
Successful opportunity teams continually evaluate what buying groups
likely doing/thinking/feeling at current juncture asking themselves what
would prove most valuable right now paving paths simplifying
complexities clarifying ambiguities fostering empathy/connections vital
advancing initiatives effectively achieving milestones crossing roads
together successfully!
Strong teams relentless dedication towards strategy work unfolds within
win rooms where initiatives ranging from scoring mapping relationships
developing strategies engaging executives analyzing competition
blocking pre-call prep occur—all momentum generated here forms
foundation future successes achieved through collaborative efforts
across board members contributing skillsets collectively nurtured growth
potential realized beyond expectations met consistently always striving
excellence driven outcomes achieved together ultimately celebrated
later down line too!
10. Celebrate And Follow Your B2B Big Deal Sales Playbook
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 Securing big complex contracts could span months—even years—
once victory achieved celebrating wins essential not only
rewarding commitment dedicated efforts but reinforcing successful
habits cultivated throughout organization culture!
Company leaders recognize appreciation serves powerful motivator
while celebrations deposit resilience bank accounts integral win culture
amplifying narratives journeys traversed across organizations leading
more significant deals secured eventually down line too!
One simple method many clients employ entails ringing bells real bells
offices emailing ring-the-bell notifications each closure celebrated
similarly fostering excitement unity amongst colleagues ensuring
everyone acknowledges contributions made along way experiencing
various triumphs collectively shared!!
Clients closing millions dollars utilizing plays outlined during course
enriched opportunities presented following training programs focusing
customer acquisition expansion key accounts gaining traction popularity
amongst VP sales aiming land bigger contracts securing larger revenues
generated guiding principles employed throughout endeavors pursued
consistently adapting various methodologies aligned current trends
shifting needs observed within marketplace itself continuously evolving
strategies met effectively addressing challenges overcome paving paths
forward instead finding stagnation stifling growth potential realized
together collaboratively advancing success stories shared across
networks influencing broader communities surrounding ventures initiated
sustaining momentum fostered continual improvements witnessed
collaboratively achieved outcomes!!
If seeking additional resources check out books “Top Sales Leader
Playbook: How Win 5X Deals Repeatedly” alongside “TOP Seller
Advantage: Powerful Strategies Build Long-Term Executive
Relationships”! Alternatively explore valuable tools accessible website
while following me LinkedIn where regularly posting updates regarding
current effective practices within B2B strategic sales arena announcing
newest courses available via LinkedIn Learning platforms cheering
successes achieved following winning plays driving growth closing 5X
deals!!