2020. What a strange year.
Okay, so it’s probably better to keep most parts of 2020 in the
rearview mirror. But there have to be some positives from the year,
something to take with us into 2021 that will serve us well. What did we
learn in 2020? (Besides the wonders of contactless pizza delivery and
working from home in sweats.)
The Proposify sales team spends all day, every day working deals and
working to get better. With all the changes going on in the greater
world, there have also been lots of pivots within the team and their
processes. So I asked our sales team: what’s one thing you learned in
2020 that you’ll be taking with you into 2021?
Now I’m turning this post over to Devan, Colin, Gabby, Scott Y., Scott T. and Will to share their lessons learned in sales, enablement, operations, business development, and management.
1) Even trainers need to learn something new
I’m one of those who did a full career pivot in 2020. I left academic
teaching for startup teaching and, boy, is that a difference!
- Embrace the chaos
Scaling in academia meant surviving those horrible 300-student lectures. Scaling now means making everything available online so that our sales reps can learn whenever they take the time. What that de facto means for me is that I never know when I suddenly have to grade an assignment for a course I haven’t looked at in months. What were they supposed to learn again? It’s chaos and it’s challenging and it’s also kind of the best thing about the model because I constantly have to refresh my own knowledge.
- Script, script, script
I thought I’ve done it all: workshops, lectures, interactive classes. Nope! Videos are a whole different beast. Gone are the days that I throw a few bullet points into the speaker’s notes and wing it to the feel of the room. In a video, that leads to rambling and horrible pacing, so now I write out scripts for everything I say. While that was a hard shift for me, it helps me understand my reps more since they work off scripts, too.
- Power? What is power?
When you’re teaching in academia you are the boss, like it or not. I never liked the hierarchy but it did make sure that my students hand in assignments on time and stick to the schedule. My reps would laugh about that. I don’t have any power, but what I do suddenly have is a sideline as my own personal marketing department so reps get excited to take the courses and stick with the assignments.
All in all, 2020 taught me to be a better planner, writer, and marketer!
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2) Find the balance between solving problems and preventing them
In 2020 I learned that you have to find a balance between putting out
fires and preventing them. And let’s be honest, there were a lot of
fires in 2020. My goal is to always make sure that all processes are in
place so my team can focus on what they do best, which is selling. This
means I spend a lot of time analyzing what processes are working, what
needs to be fixed, and what processes should be implemented that will
lead to happier reps and more sales.
However, as much as you plan, problems will always arise and Sales
Operations is the first team reps will go to for technical support,
process problems, etc. But how can sales operations make sure to protect
their time to ensure they’re playing a more strategic role? Here are my
- Protect your calendar and schedule times for specific tasks. It
feels good to help someone out as soon as they come to you with a
problem or bug they found in the CRM. But this is not productive and
will hinder long term success. That’s why I started blocking off time in
my calendar dedicated to ‘fixing bugs’ or filling requests from the
rest of the team.
- Proactively look for bottlenecks,
redundancies and time wasters. Then, make sure you dedicate time to
this. That’s right, add another block to your calendar for planning,
project work, strategic thinking, etc. The goal here is to make sure you
are focusing on preventing fires and not spending your whole day
putting them out. I like to turn off all notifications during these time
- If one person is struggling with something, chances are, so is everyone else. If a rep comes to me with an issue they are having, I like to record a video and send it to them. I then upload that video to our training software so that it’s searchable by the whole team. This teaches your reps to be resourceful, rather than coming to you every time they have a problem.
Now, I’m not perfect at any of these. I am a helpful person by
nature, which means I like to solve problems right away. However, the
above tips help make sure that I’m balancing time between fixing
problems today and eliminating future problems.
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3) Don’t freeze up over cold calls
I learned a lot this year. Having just started at Proposify last
January, my expectations of the year were pretty different from the
This is the year I made my first cold call. So, how do you make a successful cold call? Here’s some of what I’ve learned:
- Your script - Have a script nearby you can reference, pretty
soon you'll have it memorized but it eases the jitters and it's great
for when your mind goes blank!
- Roleplay - Ask your manager
or other reps to roleplay cold calls with you, do it over Zoom with
cameras off to simulate a real call. Practice the first half a few
times, the middle, and the meeting ask.
- Call review - Review
calls with your manager, it's great to recognize what you did well and
what you need to work on. This will also help you figure out what you
should be roleplaying! (P.S.: It’s okay, no one likes the sound of their
- Calendar- Block your calling times in your
calendar! This time is precious and shouldn’t be interrupted. Protect
this time because this is your money-making hour!
- Keep going - this one is easy. You had a bad call? Move on to the next. You booked a meeting? Keep the momentum and keep calling.
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4) More is more when it comes to questions and creativity
2020 taught me two important things: you can’t make assumptions and sometimes you have to get creative to get the win.
- When it comes to the decision process, assume nothing.
2020 threw a lot of wrenches into a lot of plans. When it came to demonstrating value and navigating the financial and decision processes of prospective clients, any predetermined notions of signing authority went out the window. It became even more important to discuss this early and often with prospects to understand what was needed to get a deal done. This was a great learning and gave many of us a strong foundation for these important conversations in 2021.
- Creativity in cycles wins business.
Leveraging video in emails and in proposals helped win three of my top deals in 2020. It allows for personalization, reiterating how problems can be solved and can help separate you from the competition. Sending a vacation-themed video to the president while they were on vacation definitely took the cake!
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5) When the ‘best practices’ don’t fit your reality, make your own blueprint
In 2020 I learned a good framework is more valuable than a blueprint.
Blueprints rarely account for everything going on with your company’s
specific scenario and generally, anything you try to implement has to be
tweaked to some degree. Not to mention, no one had the blueprint on how
to overcome what we experienced in 2020: a global pandemic, racial
injustice, and a presidential election. Phew!
3 ways frameworks were useful:
1. Building a sales playbook
It’s a bit of a daunting task to build a sales playbook from scratch.
I knew some pieces I wanted to include from talking to the team but
wanted to make sure I wasn’t missing anything monumental. I reviewed one
of Kevin Dorsey’s
presentations on building a playbook and realized by creating a
framework of what we’re already doing today and fleshing those areas out
in detail, I’d have a really great version one. This helped me keep
things simple and get something into the reps’ hands they could use
immediately and we can build upon together.
2. Coaching remotely
Having moved from a team lead role to full-on management in
September, I needed a completely new framework on what I should be doing
day-to-day. It was hard to find resources that both reflected the
current reality and were fully applicable to my role. So—a framework.
I asked myself, what are the key activities that will contribute to my team's success? Based on our 2020 goals they were:
- Call coaching
- Pipeline reviews
- Deal strategy
- Skill development
Once I had the framework of where I should be focusing it became
easier to lock-in and execute rather than be reactionary to the constant
changes happening within the business and out in the world.
3. Building an outbound culture
I’ll be honest, this one was probably the biggest challenge of
working remotely. How do you change the daily behaviours of a team used
to working mostly on inbound opportunities?
Well, you give reps a framework on how to do it and make it the focus of all coaching opportunities.
The sales team worked with Michael Hanson to build the outbound portion of our playbook. This gave reps a clear roadmap on how to make cold calls, write compelling emails, prospect on LinkedIn, and use video to generate interest.
There’s no blueprint that says “say this exact thing”. The reps use
the playbook to come up with their own talk tracks and ways of
personalizing outreach and they’ve really grabbed the bull by the horns.
The majority of our pipeline is now generated through outbound!
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6) In a wildly unpredictable time, your process should be as predictable as possible
2020 was a huge year for me: new baby, house, job, and car!
For sales specifically, I learned the importance of having a process.
Something repeatable, scalable, and reliable that I can make work for
every customer I speak to.
I've learned stepping outside of your set process and skipping stages
often causes some trouble either pre- or post-sales. But if you're
confident and stick to it then you'll see consistent and predictable
My process is:
30 minute disco - 60 minute demo - 30 minute onboarding review - 30 minute proposal review.
Each stage brings value to my customers and leaves plenty of time for
me to completely understand every one of the customers personal &
business problems that Proposify can solve. And it only gets better with
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