How Sales Has Changed
@ 2016 Drift.com, Inc.
All rights reserved.
Written by: Jess Iandiorio
Designed & edited by: Erik Devaney
No parts of this book may be used or reproduced
in any manner without written permission from
the copyright owner and publisher, except in the
context of reviews.
Drift • How Sales Has Changed 3
Table of Contents
Chapter 1 • How Buying Has Changed
Chapter 2 • How Selling Has Changed
Chapter 3 • Sales Process
Chapter 4 • Sales Tools
Chapter 5 • Sales Skills
Chapter 6 • Sales Measurement
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Growing up, I always looked forward to shopping trips. I say
“trip” because it was a minimum of 1.5 hours in the car to the
nearest mall. But the experience of back-to-school shopping
with so many stores and choices was a real luxury. We would
even occasionally travel 2.5 hours to Montreal to get the
“European flare” of clothing. I now know that was more about
the US to Canadian dollar conversion, but back then all I knew
was I was having an experience.
Going into our small town for the basics was one part necessity,
one part social visit with all of the storeowners. With very few
stores, the options were limited, and the relationships were key
to getting a special item you wanted.
And then I grew up.
The internet was born and access completely changed. Today,
I rarely set foot in a store. What’s more important: I don’t
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want to. What used to be a luxury is now an overwhelming
burden. Just try stepping foot in Bed, Bath, and Beyond during
the holiday season without a gameplan, with floor to ceiling
products, and not have a panic attack. Too many options; too
I just want to plug in a simple search term, one click checkout,
and get back to life. If I show up at a store, it’s because I already
know what I want, and I’m required to show up to get it.
And I’m not just a buyer of consumer products. When
purchasing products for business, it’s the same thing. I want to
do research myself without someone’s influence, find a way to
verify a product is good (from someone I trust), and throw my
credit card down.
I’m savvy, I know what I want, and I don’t want to be sold to.
I’m every buyer.
What follows is an in-depth review of how buying has
changed, how selling has changed, and how sales professionals
need to change. As demonstrated by 20-year sales veterans
from internet-based businesses, we also showcase the four
areas change has been forced: Process, Tools, Skills, and
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How Buying Has Changed
My story is not unique. Today’s buyer has access to the
majority of information they need before they even talk to your
sales team (if they need to at all).
Paco Underhill, famed shopping scientist and author of Why
We Buy (published in 1999!), said in that book:
“Few websites will permit you to see if a particular item
is in stock in a store near you, order it, pay for it, and
then go in person to retrieve it. In other words, a hybrid
Well Paco, you called it. And now it’s table stakes, and called
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“site to store,” although “hybrid cyberphysical” transaction
sounds far more futuristic.
This digital catering to consumers who know exactly what they
want is the norm.
Steven Power, President of Yodle Brand Networks, has spent
20 years selling at companies like Shell, ReachLocal, and
Bigcommerce. He very clearly articulated the change in today’s
“I think we’re in one of the most exciting and simultaneously
challenging periods for the way in which buyers have changed
in the last 20 years. The change is profound.
1) Buyers have phenomenal information. They really
understand their markets, products, services, features,
pricing, and alternatives better than they ever have. We’re
dealing with highly educated and informed buyers that are
really in control of their purchasing decision.
2) Decision-making cycles have become must faster, more
sophisticated, and more horizontally integrated through social
networks and mobile communications. People can find out
formally and informally through their networks if a company
and product is good or bad to deal with, and if they deliver,
3) I don’t think customers are sold to any more; I think they
buy. It’s much more about truly understanding a customer’s
problems and needs, if you’re relevant and appropriate, and
then helping them uncover, discover, and develop the solution
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on their terms. We’ve become guides, facilitators, and success
coaches; we’re not sales professionals anymore.”
For internet businesses, the sales dynamics have changed
significantly, especially with the advent of freemium business
Acquia, a leading cloud platform for building, delivering, and
optimizing digital experiences, operates with a free version
of their Acquia Cloud product. Tim Bertrand, their Chief
Revenue Officer, said:
“Buyers are a lot more educated when you as a seller come
to the table. A buyer 20 years ago may have picked up a
pamphlet or white paper at a conference, or found you
through an analyst or word of mouth, but there was a lot less
research they were able to do. Today, buyers have typically
done their own research, played with the product, talked to
others who use the product, and gone out and done analyst
research before you even discover them.”
The ability to “try before they buy” has become the norm
for buyers across both consumer and business products.
Especially in software where buyers not only have more access
to information, but have been burned in the past by false
Understanding in a demo that a product can conceptually meet
a customer’s needs is not enough before a purchase is signed.
They need to touch it, and maybe even customize it, before
they’re willing to part with money. But this does come with an
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advantage: Faster sales. Tim continues:
“We’ve done enterprise deals in under 60 days. It’s because
the buyer already has our product, and they’re already in a
deep decision-making cycle by the time we speak with them.
That’s dramatically changed the game for the length of the
Forrester Research recently published a complex graphic
showcasing the B2B Buyers Journey, which is how the highly
educated and experienced buyer comes to be:
Today’s education process uses all devices and all vehicles
possible. Print is almost non-existent as an influential force
(goodbye, print advertising!). Peers and social proof have
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emerged as a critical part of the entire buyer’s journey. What’s
promising for sales pros is they still play a critical role across
the awareness, research, and comparison process, not just the
transaction. They just have to play it differently.
There’s one element in this image that is hard to quantify, but
has become essential: Trust. Adam Zais, Former head of Sales
and Marketing at Wistia and Chief Revenue Officer at Robin,
has been selling over 20 years and identified the 800-pound
gorilla of today’s sales cycle:
“Sales used to be more about manipulation than anything.
Now there are no manipulation points. There are emotional
points that become levers, but they’re not about information.
There’s much more focused on trust. It’s not about likability,
it’s about trustworthiness. That’s the emotional base sales rests
on. Trust is about honesty and integrity. Differentiation is
coming down to service and trustworthiness, rather than
The manipulation of the past lead directly to buyer skepticism
that exists today. Mark Rudolph, Chief Revenue Officer at
“Traditionally a lot of buyers would spend millions of dollars
on software and it’d become shelfware and they’d never use
it. Even SaaS originally, people would be willing to buy an
annual or two year contract because the cost was so much
lower, but they still didn’t end up fully using it.”
This lead to skepticism and overall lack of trust, creating a
tough environment for reps to build trusting relationships with
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So there we have it: Today’s buyer is highly educated and
experienced. They’ve researched your products and your
competitors down to the feature level, and is likely in a trial.
They’ve also backchannel referenced your company through
analysts, colleagues, and friends. They are not out to be sold
to, they’ve shown up to buy and they’re figuring out if they can
trust you. One would think that’s like shooting fish in a barrel,
but it isn’t. Adam said he’s always coached his sales teams with
a simple phrase:
“We don’t sell things, we just help people buy.”
But, what’s the best way to help the right person, at the right
time, in the right channel?
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How Selling Has Changed
“One of the worst things to happen to sales was the movie
Glengarry Glen Ross.” -Adam Zais
For decades prior to ecommerce and the dawn of software-as-
a-service with Salesforce, “hard tactics” were lauded as the way
to sell. “A. B. C. Always be closing” is the infamous line Alec
Baldwin spoke in Glengarry Glen Ross to show hard tactics.
To counter this, Tim Hurson and Tim Dunne published Never
Be Closing. Hurson and Dunne explain that selling isn’t about
manipulation. Instead, today’s successful sales professionals are
driven by helping their customers.
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Zig Ziglar, may he rest in peace with 24 books to his name, is
credited by many for training sales reps in hard tactics such as
the presumptive close. His most famous books are Selling 101:
What Every Successful Sales Professional Needs to Know and Secrets
of Closing the Sale.
In Secrets of Closing the Sale, Zig states:
“The prospect is persuaded more by the depth of your
conviction than he is by the height of your logic.” -Zig Ziglar
This is no longer the case. Steven Power talked about the
changing nature of the salesperson’s knowledge and skills in
order to close a deal, and that it’s no longer about hiring “a big
hammer with a lot of conviction and determination”:
“The best sales reps today have high self-awareness and are
tech savvy. You need people who enjoy serving and helping
solve problems, even more than they want to close deals.
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They need to be able to help people see and understand your
solution, how it’ll work for them, and why doing business
with you is fundamentally better. They need to be thought
leaders, evangelist, and technically adept in order to convince
Salesforce not only created
the new SaaS world, but they
also used what they learned
and told sales professionals
how they should operate in
it. Aaron Ross (Formerly
Salesforce, now founder of
Predictable Revenue, Inc.),
and Marylou Tyler (CEO of
Strategic Pipeline) published
Predictable Revenue: Turn Your
Business Into A Sales Machine
With The $100 Million Best
Practices Of Salesforce.com in
2008. Every single person
I interviewed for this book
referenced it as essential reading for salespeople today.
I had the opportunity to interview Will Anastas, SVP
Enterprise Corporate Sales at Salesforce, to learn how selling
at Salesforce has evolved even beyond the lessons in Predictable
“Today salespeople need to differentiate themselves at that
initial point of contact, not so much by product or company
reputation, but by what real business problem they can
Drift • How Sales Has Changed 15
solve. One thing we’re really focused on is how we can create
authentic experiences, based on building an understanding
of our customer’s customer. We’re training our sales team to
experience what it’s like to be a customer of our prospect before
we walk in the door.
“Last week a sales rep was preparing to pitch a high-end
women’s retail brand, so he went to the store, bought a
blouse, and returned it. He did the same thing online. He
was able to come to the meeting with real-world examples
of their customer experience, and how we can improve it.
Next week I’m visiting a gas company. Before the meeting,
I’m riding with a gas reader, someone else is going on a sales
call, and another person is going on a ride-along with a
customer service provider. We’re not going to know how we
can help their business unless we understand their customers
Building buyer empathy is becoming an extremely key
ingredient, especially to enterprise SaaS sales.
Ashley Welch spent 20 years in sales before co-founding
Somersault Innovation, which takes the principles of human-
centered design into the sales process. She trains sales teams
on how to be truly curious, empathetic, and customer-centric.
She points out that traditional approaches like BANT (Budget,
Authority, Time & Need) for qualification come hand in hand
with staged questions that serve the seller first, buyer second.
“There’s a difference between being genuinely curious
and asking questions about the customers pain, and only
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expressing curiosity by asking questions that relate to what
a rep wants to sell. That’s not really about being open and
curious. We need to help reps understand what’s genuinely
curious and open versus when they’re sticking to only their
What Ashley focuses on most is getting an organization to
change their DNA and start to think and operate differently.
Being customer-centric has to go beyond individual sales tactics
and into sales management.
“We start from the leadership down. We encourage sales
managers to rethink their pipeline review meetings. Instead
of starting with “What did you sell today?” the dynamic of
that meeting has to change. Large group calls where everyone
is hammered on what they close and what stage their deals
are in are dying. They reinforce the bad behavior which is:
Close, close, close. Instead, sales leaders are encouraged to
kick off their meetings by asking what their reps learned
about their customer’s customers. This reinforces and rewards
curiosity and empathy, not just sales performance.”
It’s only natural that with a role undergoing such
transformation that the management of that role will need to
adapt to change as well. Let’s look at how the change in sales is
occurring across sales process, tools, skills, and measurement.
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Thanks to our friends at Sales Benchmark Index, here’s a
typical lead funnel chart:
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What’s changed? Demand Generation, The Marketing-
Captured Lead, and the Marketing-Qualified Lead.
Freemium models now introduce the new funnel: Product-
Qualified Leads (PQLs). In this world, marketing typically
executes an inbound marketing approach using content to raise
an organization’s visibility, and converts prospects to a free trial
account. This is all still considered top-of-the-funnel activity for
marketers. But people downloading white papers are no longer
considered marketing-qualified leads, and no longer passed
directly to sales. This reduces the amount of leads coming in,
but what the sales team gets in return are more highly qualified
leads. The middle of the funnel is now where all the action
is, and sales reps needs to get comfortable onboarding and
activating free trialers so they can become product-qualified
Tom Wentworth, Chief Marketing Officer of RapidMiner
(Former CMO of Acquia and Ektron), wrote about why he’s
killing the MQL in favor of the PQL.
“There’s no arguing that the MQL, and the broader sales
and marketing funnel, transformed marketing. It forced
alignment, requiring sales and marketing to agree on the
traits and actions that made a good lead. It required a good
content strategy to guide prospects through the complex B2B
buying journey. It drove a consistent set of lead management
processes that made it easy to measure conversions at key
points. And maybe most importantly, it let marketing prove
our contribution to revenue.
“I loved the MQL. I owe my marketing career to it. But now
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I’m over it. I’ve learned that more isn’t always better, and
I think the MQL treadmill is slowly starting to suck the life
out of marketing.
“Enter the PQL.
“I first heard of the concept of a PQL — or product qualified
lead — via Christopher O’Donnell of HubSpot via a post on
the excellent OpenView Medium publication. The basic idea
is to combine freemium/open source product distribution with
an inside-sales model to increase deal velocity. Users qualify
themselves by using the product and inside sales exists to
support them through the journey and set the stage for a long
term relationship with the customer.”
(Image source: OpenView)
The material impact on the sales process is it no longer needs
to involve cold calling our outbound marketing, if you’re doing
it right. It’s less about opening up your daily lead funnel and
sending out tons of emails and calling people, and more about
reaching out to help trialers get started and be genuinely
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What this requires is extensive knowledge of the solution, what
it can do, all of the features, and how they work. PQL cycles
can take two paths to conversion:
1. Self-service conversion
2. Sales-facilitated conversion
Self-service is for buyers who know they want or have to pay for
your product to keep using it, and online offerings meet their
needs. It’s as simple as using their credit card.
The sales-facilitated conversion also has process changes. Not
only are you contacting someone only after they’ve already been
at least intrigued, if not sold on the value promise, but your
main job is now to get them to see that the product delivers on
its promise from a functional and value-based perspective.
Chris Anderson, famed author of Free: The Future of A Radical
Price, The Long Tail: Why The Future of Business is Selling
Less of More, and, most recently, Makers: The New Industrial
Revolution, had the foresight to know not all free customers are
created equal back in 2009:
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“It turns out not all free customers are alike, and what they’re
worth to you depends on when they arrive. In the early stages
of a company or product, when it’s trying to get traction, free
is the best marketing.”
So it becomes sales job to differentiate one free customer from
another to figure out who to spend time with. Additionally, the
type of freemium model drives different prospect behaviors:
“The Problem with (time-limited) free trials is they
discourage full participation during the trial period: Why
spend a lot of time learning to use something when there’s a
chance that when the time comes to pay you may not feel it’s
worth it? Indeed, why start using it at all?”
So sales needs to figure out not only who to spend time with,
but also how to get them to invest in the time-limited free
program to get the product-qualified.
In addition to time-limited, Anderson presents three other
freemium models which all pose their own strengths and
challenges: feature-limited, seat-limited, and customer type-
limited (big or small, etc.).
Phil Harrell, Leader of SiriusDecisions Chief Sales Officer
Strategies practice, talks about the nuances of qualification
within the freemium model:
“I grew up B2B sales when the salesperson had more
opportunity to qualify via human interaction. Now there’s
a lot more digital interaction. The buyer is doing a lot more
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online without talking to someone. Organizations need to set
up digital qualification criteria that reads a free users digital
body language, and decide what indicates propensity to buy.
Companies and salespeople need to find ways to see when
a prospect is raising their hand, without them raising their
This is a massive process change for sales reps to get a handle
on. It also can’t be done successfully without harnessing new &
emerging sales tools.
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While new sales tools are emerging daily to help the modern
sales rep, the good news is most are free(mium)!
Today, you can find free CRM tools, email finders, and you can
even get rich prospect profile data with pulls together social &
company information on your buyers. It’s never been easier to
find people, and find out more about them.
But there’s been a new category of free sales tools cropping up
that really help a rep shift from selling to serving. Here are the
top four service-oriented sales tools that help you better connect
with and drive value for a prospect:
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1. Live Chat Software:
Messaging is eating the world
of business communication. I’ve
known many sales reps who
connect with prospects and
customers over Skype or Slack to
offer real-time communication
- but that’s only great for once
you know who they are and
have a relationship. Prospects
who come to your website and
are unknown also have the need
for real-time communication.
Live chat software puts sales
professionals in a purely helpful
role. Companies like Drift
(shameless plug) and others
offer free live chat products to
immediately get the conversation
started and help a prospect get
the information they need.
2. In-app Usage/Analytics: It’s hard to know whether a
prospect has started using the free trial product, unless your
team baked that into the functionality, which probably didn’t
happen. What you need is context around who’s signed up
but is inactive, vs. who’s active, to play the right helping
role. Companies like Mixpanel provide usage/analytics data
which can trigger information into the sales reps hands to
immediately have the right conversation.
Drift • How Sales Has Changed 25
3. In-app Messaging Software: Tired of sending emails that
don’t get opened? Those days are gone if you employ an in-app
messaging solution that gets seen 100% of the time a prospect
logs into your tool. It keeps your messages brief & helpful.
4. Social Selling Tools: Serving prospects isn’t just about
helping them understand and use your prospects, it now
expands to how you can enrich their life. This largely happens
through reading what they read, and sharing what would be
useful to them through social media. This blog post showcases
5 disruptive social selling tools that help you exponentially
increase the value you provide a prospect above and beyond
your product & service.
Jill Rowley, employee #13 at Eloqua who built the marketing
automation space and now is the foremost expert on social
selling, recently contributed to the Mikogo blog “Sales Trends
in 2015 - Predictions by 14 Industry Experts.” She wrote:
“I am hopeful for a mindset shift from selling to serving.
Sales professionals need to move from using LinkedIn as their
online resume, to managing their digital reputation. Instead
of optimizing for the recruiter; optimize for the buyer. Here’s
• It’s no longer Always Be Closing; it’s Always Be
Connecting. Your network is your net worth. Nobody likes
to be sold to. We’re living in the Age of the Customer where
buyers have choice and voice.
• Sales professionals need to read; read what their buyers read
and share that content across their social networks.
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• Sales professionals learn how to listen; listen to the
conversations being had on the social web. Social Selling is
about finding and being found. Social Selling training for
your Sales team is NOT OPTIONAL because a fool with
a tool is still a fool. Oh, and if you suck offline; you’ll suck
MORE online. #Don’tSuck.”
Tom Murdock, AVP of Sales at Fuze, has been scaling
inside sales teams his whole career, and has made significant
investments in social selling tools and measurement:
“We’ve implemented a social selling index at Fuze. I think
it’s really important that reps be seen, in the earliest days of
the sale process, as a thought leader beyond your products.
We know that sharing helpful content about our market in
our networks is well-received by the buyer because it shows
we’re in-tune. We’re assessing our reps on how well they’re
connected to buyers that could influence opportunities, and
how good they are at selling and influencing in channels
beyond phone and email.”
These service-oriented sales tools help sales reps help prospects
in an extremely valuable, real-time, and contextual way.
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The way I researched the change in sales skills was to asked
everyone I interviewed: “What do you look for when hiring a sales
Unanimously, SVPs & CROs do not look for length of
experience and an extensive “rolodex.” They don’t even look
to hire from competitors anymore. The new criteria are
simultaneously soft and hard:
“We hire people that are intellectually curious, passionate,
want to work hard, and smart. Those traits far outweigh
someone that has a rolodex.” -Tim Bertrand
Drift • How Sales Has Changed 28
“I always look for the intangibles. I don’t care if they come
from the industry. I don’t care where they went to college.
What I care about is: Are they smart? Are they driven? Do
they have the right work ethic? You can’t teach that stuff.
I can teach you how to sell, and I can teach you about the
product, but I can’t teach you to be totally psyched to get up
every day and go out and make money. Work ethic, desire,
grit, scrappiness, genuine curiosity and the ability to get
creative I value a lot more than if they went to an Ivy
League School.” -Will Anastas
“We hire people with high self-awareness.” -Steven Power
“I hire people who want to help people. At Wistia instead
of sales their title is ‘Customer Happiness.’ Instead of
writing champion letters, they’re helping people with the free
product. Some may say that’s not a sales activity, I say it is.
Everything you do today is about earning the right to have
that customer tomorrow.” -Adam Zais
“I’m looking for someone that can demonstrate a willingness
to self-invest. That might be the person that put themselves
through school, is taking night classes, or did something to
improve themselves. I think that sales and the marketplace is
constantly changing, and you want someone that’s willing to
evolve with the market. Not only is the sales model changing
but the product is constantly being innovated and iterated on,
so you need that person who’s not only curious but interested
and invested in learning.” - Mark Rudolph
“We hire people who are tech savvy. People that come from
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a service/technical background often make the best sales guys
because they know what they’re actually selling.” -Steven
“The most successful sales guys are tech savvy and completely
up to speed on the product and able to go toe-to-toe with any
prospect, without needing pre-sales or solution architects in
the room to answer questions.” -Tim Bertrand
It’s clear: High EQ (Emotional Intelligence Quotient), tech
savviness, and desire to help, combined with the classic work
ethic, are required today.
But there’s one word that didn’t come up that I know they
all would have said “Yes!” to, and it’s debatable if this is a
personality trait or a skill: Empathy.
When asked what books he’d recommend new sales reps to
read, or not to read, to succeed in sales today, Will said:
“There’s one book that transformed
my thinking about how we
can understand our customer’s
customers. Brené Brown’s book
Daring Greatly: How the Courage
to Be Vulnerable Transforms The
Way We Live, Love, Parent,
and Lead, is actually perfect
for sales today. You have to be
vulnerable and put yourself out
there to understand your customer’s
customer and establish empathy.”
Drift • How Sales Has Changed 30
Understanding buyer psychology is not necessarily new, but
looking at your own psychological behaviors and how they can
impact sales process can be groundbreaking in enterprise sales
Drift • How Sales Has Changed 31
With the sales role transforming, measurement also takes on
a new life. It’s no longer black and white. It used to be “You
made your number or you didn’t.” But there are new (added)
1. Real-time engagement
2. Social engagement
3. Free trialer activation
4. Free trialer conversion
Note: You can also add to this list a (highly qualitative)
measurement of whether a salesperson is able to build trust.
Drift • How Sales Has Changed 32
1. Real-time engagement: This is measured through response
time. It’s easy to measure via live chat software. It’s widely
known that you have just under a minute to respond to a live
chat from a prospect before they leave, so set your sales rep
2. Social engagement: If you can assess a company’s social
brand, you can also assess an individual’s social presence. Klout
is a widely known measurement tool for social brands, but if
that doesn’t work for you, check out any of these free tools.
3) Free trialer activation: Lincoln Murphy, of SixteenVentures,
writes extensively on freemium models, and conversion rates.
He points out activation is a vanity metric if you’re only
looking at log-ins, and each organization needs to establish
what meaningful activation is - whether it’s usage of 5 or
more features, submitting a support ticket, or something else.
And then you have to monitor transitions between active and
inactive usage patterns which affect potential conversion.
4) Free trialer conversion: Rather than purely showcasing
if a number is hit or not, sales teams with freemium models
now have a freemium conversion goal based on the number
of trialers who transition to paying customers. While the
conversion target freemium to paid is a heated debate, most
organizations expect at least 5% to convert, and some get
towards 10%, there’s an active debate on why a conversion rate
this low should be the norm.
5) Retention: There used to be a divide between account
executives (new business), and account management (customer
renewals). The AE’s job was to land the customer at the highest
Drift • How Sales Has Changed 33
price possible, the account manager’s job was to make sure the
organization delivered and the product/service was used.
This still exists at many organizations. But the lines are now
blurring. It is not uncommon today to see roles where an
individual’s success is also tied to the retention rate of those
customers he or she originally sold.
With a slant towards service instead of sales, the customer
success role has emerged which is one part service, one part
upsell/cross sell sales. This new role reduces (and maybe even
requires) the sales reps’ need to land one big upfront deal in
favor of landing many small deals that can be safely delivered
upon, and the relationship grown over time.
Drift • How Sales Has Changed 34
It’s a whole new world for a salesperson today operating at
an internet business. Hard tactics, Rolodexes, and extensive
experience with enterprise sales cycles are no longer valued.
Those who bring tech savvy, emotional intelligence, and a
genuine desire to help people will be handsomely rewarded.
Thanks for reading. Click here to learn more about Drift.