50 Sales Lessons from 3 Years in B2B SaaS

50 Sales Lessons from
3 Years in B2B SaaS
Evan Lewis | @evanlewis_
Director of Sales, PostBeyond Inc.
January 2018

First-Hand
Lessons & Tactics
from My Startup
Sales Journey
My first startup failed because we didn’t validate what we were
building. I coded too much and didn’t really sell. I learned the
hard way that sales is a crucial skill set for all entrepreneurs.
Since then, I’ve spent the past 3+ years in the sales trenches,
specifically in B2B Software-as-a-Service at PostBeyond.
These are my top takeaways and lessons learned. I hope you
find them helpful and are able to put some of the tactics to use!
- Evan
3 Y E A R S , 1 0 0 0 ’ S O F M E E T I N G S & C A L L S ,
D I S T I L L E D I N T O 5 0 S O U N D B Y T E S

S A L E S
O P E R AT I O N S
D E A L C Y C L E S
& C L O S I N G
S A L E S
M A N A G E M E N T
P O S T- S A L E S
A L I G N M E N T
Core Focus Areas

© PostBeyond Inc. Strictly Confidential. Do Not Distribute.
Part One
Deal Cycles &
Closing Tactics

Don’t start any sales
call without…
5 Probing Questions
1 Goal in Mind
Stakeholder Research

6
Get excited! Smile 😃
Your positive energy rubs off on
your prospects.
Be polite, complimentary,
and highly personal.

Have a pre-call routine that gets you
in the right performance mindset.
Personally, I stretch for 2mins"
Treat each call like a sporting event
where you need to perform.

8
Set an agenda at the start of
each call and ask for feedback.
“Is there anything I missed that you want to
make sure we cover?”
Credit: John Barrows

Multiple stakeholders on the call?
Have specific questions prepared for each of them.
Get them talking early, especially
key decision makers.
Go out of your way to show that you’ve done your
research and you respect their time.

10
Ask concise, one-sentence questions.
Avoid the temptation to lump multiple
questions into one jumbled thought.
Write your individual questions down
ahead of time. Practice your delivery.

After you ask a question,
learn to love silence.
🤫
Cherish it.
Let it simmer.

Video works. Period.
Put yourself on camera.
You’ll build stronger
relationships, guaranteed.
Products To Check Out: Vidyard, Zoom

Build some healthy
skepticism into your
sales approach.
People will waste
your time if you let them.
Hold buyers accountable
to their commitments. If
they don’t follow through,
they likely aren’t real.

14
With every customer touchpoint, use one
simple question to guide you:
“Am I adding value?”
If not, go find some. Don’t just follow-up.

Kill the phrase
“following up” from your
vocabulary.
Continue the conversation
instead.
Credit: John Barrows

Avoid just “sending
more information”
when you can.
When you do, use
analytics to understand
your prospect’s intent.
Products To Check Out: LinkedIn PointDrive, SalesLoft, GoVideo

In every deal, ask yourself:
“Do I have an ally or
mobilizer on the inside?”
Ally / Mobilizer (n):
Someone who pushes the deal forward, gives
you the inside scoop on stakeholders and lays
out the steps you need to take to win.
Your deal cycles will
be shorter for it.

Having trouble getting up the
chain to decision makers?
Ask your prospect about them.
“Have you talked to X about this project?
What was his/her feedback?”

Make it easy for your
prospects to buy.
Build a business case
that they feel confident
selling internally.
💼 Business Case Components ✅
1. Customer Pain To Be Solved
2. Program Objectives
3. Technology Overview
4. KPIs / Success Measurement
5. Stakeholders Involved
6. Implementation Plan + Timeline
7. Case Study w/ Similar Customer
8. Pricing & Scope
9. ROI Breakdown

20
Always anchor your business case to
the customer pain 🤒
Get the prospect to answer these questions LIVE
on a call while you play scribe:
1) The problem we are aiming to solve is…
2) This problem is stopping us from hitting our goal of….
3) This problem is a priority now because…
2) If we do not solve this problem now, we will…

If a buyer doesn’t grant you access to
meet with other stakeholders who
need to be involved, they likely aren’t
serious about doing a deal.

If your prospect…
1) Looks nothing like your existing successful customers
(industry, size, use-case, persona)
2) Is saying all the right things and insists they can move
quickly and skip steps in your sales process
…you shouldn’t count on them closing.

Strive to have a VP-level champion
or above in every deal.
Watch your deal cycles shrink!

Avoid letting weak champions
sell on your behalf.
Ask to be in the room 💬
If their boss picks holes and you aren’t
there to push back, you’re going to lose.

☎ Dial at off-times of day ⏰
Catch people when they
have a free minute –
5:30-6:30pm on the drive home
usually works well.

26
Need more intel on where you stand in
a deal and what you can do to help?
Use unconventional channels to
communicate with stakeholders.
Friendly Twitter DMs, texts and
LinkedIn messages are 👌

Sticky situation on an email thread?
Unclear of what the prospect means?
Pick up the phone!!!
It is easier to talk it out live than to
wordsmith and hope for the best.

28
When talking about price, have a
frame of reference for what your
prospect could spend. Use other
technologies or services they have
purchased as benchmarks.
Never price low out of the gate
if you don’t need to.

Practice your pricing delivery.
Be as frank, clear and nonchalant
as possible.
Credit: Chad McCaffrey

30
Learn your buyer’s fiscal year-end.
Ask if they have discretionary budget
mid-fiscal. Prioritize your pipeline
accordingly.
As much as you want to, you can’t
force people to buy when the money
simply isn’t there.

Lay out your next steps.
Be prescriptive.
Help the buyer understand
why the next step will be
helpful for them.

Always have levers you
can pull in negotiation.
Think ahead and chart
your Gives and Gets.
Credit: Taylor Coulis

33
Get confirmation on pricing
boundaries from your boss.
It helps with your confidence and
delivery when you are 100% sure
what your options are.

Play the man behind you.
When it comes to holding firm
on deal terms, make your boss
the bad guy.
Credit: Chad McCaffrey

35
Anticipate roadblocks or slowdowns
in your deal cycle.
Ask your champion for permission to
get ahead of them.
Common Slowdowns:
- IT evaluation
- Security questionnaire
- Legal MSA review

Stalled deal? Call-outs work 📣
If prospects aren’t delivering on their
commitments, don’t be afraid to call
them out politely.
If they can’t handle the truth and own up,
you know you don’t have a real champion.

Think like a marketer.
As a salesperson, your
personal brand matters.
Prioritize creating
original content to
establish your voice.

38
Make time for social 📲
Build a social selling routine
that fits with your schedule,
and stick to it.

Part Two
Sales Management

Recruit and screen new hires
against clear success criteria.
Don’t hire for the sake of
hiring. Set the bar high and
keep it there.
Credit: Kyle Norton

Pipeline is precious.
Before passing deals to new reps,
do your best to certify them.
Run them through mock deal cycles
with coaching throughout.

Your team is a reflection of
you and your attitude.
Bring the energy and positivity,
every single day.
Credit: Kyle Norton

Prove you can get new
reps to productivity &
quota attainment before
hiring in bulk.
It is better to have a few
reps getting FAT than
many who are starving.

Build call recording
and coaching into your
sales culture.
Circulate recordings
with your marketing
and leadership teams
to help everyone
understand buyer
behaviour and pain.

Make a habit of deconstructing
Closed/Lost and Closed/Won deals.
Look for patterns.
Fill the glaring gaps and
double down on what’s working.

46
Make clear asks of marketing.
Their job is to make sales easier.
Hold them accountable.
Better yet, collaborate!

Small and frequent SPIFs
are helpful.
Make it easy for your reps to feel
like they are winning.

Part Three
Sales Operations

49
Prioritize your Salesforce hygiene
from Day One.
Opportunity records should be sacred
and have strict rules for upkeep.

Track days in stage and diagnose what a
“good” deal looks like 📆
ie. Discovery – 10 days, Evaluation – 30 days
If a deal is taking longer in a specific stage,
that is a good trigger to dive in and
understand why.
Credit: Randy DeHaan
Product to check out: InsightSquared

Track revenue
per lead.
It will help you
understand
sales efficiency.

Map your buyer’s
journey end to end.
Set your Salesforce
stages to align with
key milestones in
their journey.
Image Credit: Jacco van der Kooij

53
Depending on your stage, consider
what is more important to you –
revenue or logos?
Set your pricing strategy accordingly.
Make sure you aren’t pricing yourself
out of conversations with logos
you’d love to have.

When it comes to target industries,
less is more to start with.
Prove that you can own ONE first,
then broaden your reach.

Part Four
Sales Alignment with
Customer Success

56
Be diligent about mapping
your post-sale handoff
process. Make sure that
expectations are clear for
the AE and the CSM.

As a sales rep, stay close to your champions
and closed deals.
Nurture those relationships and keep tabs on
how the customer is doing with your product.
If they aren’t seeing success and you haven’t
kept in touch, they will be at risk of churn.

Thank you for reading!
Let’s keep in touch.
ü Tweet @evanlewis_
ü Add me on LinkedIn
ü Email evan@postbeyond.com

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