In order to engineer a move upmarket, SaaS companies need to tailor both their sales services and people to deploy a more comprehensive or expensive service offering. Engineering this full-scale pivot includes tackling many challenges; from understanding different service requirements, tackling new processes in departmental selling vs large scale deals, to identifying the right people needed to close such multi-million dollar deals. This interactive workshop discusses the key challenges involved in cultivating the people and processes needed to smoothen this transition from mid-market to enterprise. Lukas Hertig, SVP Bizdev at Plesk, Investor and Advisor to startups, shares his business development playbook from the last 15 years, including real-life business cases to ensure your sales teams are equipped with the practical strategies needed to sell and succeed.

1. SVP BizDev@Plesk | Advisor to SaaS Startups such as Chainstack | Scaling Tech Businesses | Investor
Lukas Hertig
Moving Up Market Bootcamp
Salespeople and Processes Needed to Close Multiyear Enterprise Deals in SaaS
Note: some mentioned techniques are trademarks of their respective owners.
Linkedin: linkedin.com/in/lukashertig eMail: lhertig@plesk.com

2. A Few Words About Me..
Working with a few startups
to support them on their
journey, mostly in the
blockchain, Cloud/SaaS &
eCommerce space.
16+ Years in int. Sales,
Management, Digital Marketing &
Business Development with
120M$+ ARR Subscriptions
Based in Zurich and Barcelona
Advisor, InvestorPlesk | cPanel | SolusVM
Sold millions of $ subscription
software and cloud platforms
to global service providers
Chainstack
Cloud/Blockchain/eCommerce
LinkedIn: https://www.linkedin.com/in/lukashertig/
Twitter: https://www.twitter.com/LukasHertig
Facebook: https://www.facebook.com/lukas.hertig
Built up a digital marketing
growth team from scratch
with 30+ people
Built many global
Partnerships with Amazon,
Microsoft, Google, HP, IBM

3. Agenda
• 30 mins – Moving from a transactional SaaS model for SMBs towards an Enterprise Sales Model
• 30 mins - split into groups to brainstorm challenges and opportunities
• 20 mins - each group presents back what they have discussed & Q&A
• 10 mins - sum up with key takeaway points and learnings (free handout!)

4. 4
Bootcamp Focus: Elephant & Deer «hunting»

5. 5

6. 6
History of Selling to Enterprise..
2010VALUE SELLING
«TAS»

7. 7
Startegic Enterprise Sales for SaaS - Framework
1. RELATIONSHIPS
a. Political Map
b. Stakeholder
Management
c. Insight
d. Integrity
e. Influence
2. STRATEGY
a. Early Engagement
b. Selection Criteria
c. Competitive
Differentiation
d. Politics
3. VALUE
a. Strong Business
Case
b. Enable Revenues
c. Save Costs
d. Compelling
technical solution
4. PROCESS
a. Budget
b. Procurement
Process
c. Compelling Events
d. Capabilities to
Implement

8. 8
The Framework is a Combination of Modern Enterprise Sales Techniques
AND

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Solution selling is based on the
premise that salespeople should lead with
open-ended questions designed to surface
recognized customer needs and respond to them with a solution…
…in addition, Insight selling rests on the belief that salespeople
must lead with disruptive ideas that will make customers aware of
unknown needs.
Plus - Most sales reps rely only on the customer to coach them
through a sale & process; star reps
also coach (not push!) the customer and are perceived as
trusted advisor

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Non-traditional sales approaches dominate SaaS today – but some balance is
required!
?
Cloud/SaaS approach

11. 1. The Sales Team – People required to
sell enterprise deals
(or: requirements for a founder interested in selling to enterprise customers)

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Skills of a «dream sales rep» for value selling ☺

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Different Sales People for Different Sales Jobs..
New «Hunting»(Traditional
«Hunting»)
New «Farming»Massmarket

14. 14
Sales Skills of a consultative/value vs transaction sales person

15. 2. Building Relationships with Enterprise Customers
People

16. 16
Demand & Product
UI/UX SALES, BRAND CONSOLIDATION INNOVATION
Top Management
COSTS REVENUES
Product Managers
VP/SVP Products
Head of B2B SALES
Head of Marketing
System Administrators
IT Director
CIO
Enterprise Architects
CFO (partially)
CSO
CMO
CEO
Who We Sell to? Find the right personas to target for demand
generation..
IT
The above are just examples – it highly depends on the industry you are selling to!
Note: there are tools to find them over linkedin etc. – but use your brain! No automated reach out!

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Be a Collaborator AND a Challenger

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Try to Engage on Senior Level from Day 1!

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Finding and working with the right stakeholders and their interests

20. 20
Have a business conversation about the
customer’s business, NOT immediately about
your product/solution

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Find the right allies & get support for your idea inside
an organization and get social

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Be FAST – Speed matters!
Follow-up after Meetings:
Within 24 to max. 48 hours
by email or phone
If you cannot hold this, provide a
deadline and reach it if you set it!
Integrity matters!

23. 3. Sales Process & Building your pipeline

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Building the deal pipeline:
• Long deal cycles 9-24 months
• Focus on qualification mostly, not
just lead generation – it will save you
a lot of time.
• CAC of about 10% of the deal value
• Conversion rates of 5-10% only
• Expect a lot of work – very hard work
and a lot of rejection

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Providing Value with a
solution that may touch
many end-points or
where a competitor is
already there..
Depending on the
«Cloud/SaaS maturity
level» a customer has,
you need to think
about different
startegies & values
Decision Support tree for
defining your strategy

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Be 100% aware of the Procurement/Acquisition Process
Make sure, you find out about the official
procurement process of a company EARLY.
Talk to your business contacts about their
process, ask about financial treshholds in
terms on when an RFI/RFP process is
required and when not..
Go to meet with procurement separately if
required to find out.
This will help you in forecasting properly
and align the processes on both sides as
well as find out or even create compelling
events – such as deadlines from senior
execs etc. – what happens if middle
management will NOT reach the compelling
event? Fired? If you have aligned with
Exec level in advance, that will be your
help!

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Be There Early
Be There First
Be Faster

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Influence RFI/RFP Requirements Early – Disqualify
Competition through VALUE, not just Features

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• Assess their current organizational needs
• Immediate requirements of high priority projects – specifically around cloud and
general IT automation – whatever is end customer related
• Are there any compelling events? F.e. replacement of an existing system etc.?
• Service Portfolio definition & execution Roadmap – if existing?
• Evaluate combined solution offering – Your Saas with their business
• Functional product demonstration(s)
• Jointly work on a draft business case that includes but not limited to
o Analyze and define Potential of Churn reduction & ARPU increase
o Analyze and Define Mid and long-term objectives and related KPI’s
o Overall Cost benefit consideration
o Analyze benefits (cost reduction) by increasing level of automation and IT consolidation, now and
over time
• Combination of new solution with existing infrastructure (complementary) or greenfield
• Business Case (we can create one for them if we think it’s worth it)
• Define Enabling of Marketing, Sales, Support and Operations
Example Next Steps after the first meeting

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Note: do not offer customization pro-actively, even with big
$$ offerings. Better plan for requirements upfront and think
about integrations into enterprise systems upfront.
.. And if you hear the same story from multiple customers
what they may need as additional features, build them into
your product – and ask 1 customer to pay for it ☺

31. 5. Proposals – anatomy of an enterprise deal

32. 32
Tools: Differentation of Sales Proposals in Value Sales

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Tools: Differentation of Sales Proposals in Value Sales
• You may want to think about getting a
proposal management software
• Big $ (if 100k or even millions) –
require «proper» proposals, not just a
price list.
• Besides the proposal you often also
need things like:
• Feature Lists
• Master agreement for licensing
• Master agreement for services (if
applicable)
• Compliance proof (GDPR, SOX,
ISO and such)
• Price list(s)
• Custom license terms (if
applicable)

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Tools: The Strategic Term License (STL) aka Enterprise
Term License (ETL) – Think Big

35. 35
Group Breakout: brainstorming challenges & opportunities
Awareness Consideration Intend Decision
Prospects/Leads Qualification & Pitches Proposals, Negotiations Closing Techniques
• Ask about budgets as early as
possible and put a higher number
rather and include a lot of buffer.
• Charge like 5k «discovery fee» to
get commitment early stage – can
make a big difference in closing
rates.
• Have a strictly defined sales
process in place
• Bring in a solution architect as
quickly as possible.
• Try to parallelize workstreams
across different departments
• Create a sales funnel for
enterprise that includes many
more steps to have visiblity of
where the deal is.
• Create an initial successplan to be
transparent with the customer
about your «sales process».
• Go for the yes or not initially and
not too late in the process.
• Don’t offer customzation at all.
Call it feedback, not requests.
• If being asked for enterprise
references, try to sell to a
department first and get your
references.
• Offer a super cheap price and in
exchange they need to provide
reference calls or case studies.
• Give and take is super important.
If I’m spending lots of time – you
can provide me more things in
exchange.
• Bring in CS in an early stage
before the deal is closed
• Making decisions between upfront
and annual fees must be done
carefully. Depending on
accounting rules, company size
and so on.
• Include a lot of buffer into the
initial pricing and decide pricing
last.
• Define the timeline is helping to
close.
• 3 – 5 Points

36. 36
Group Break-out: handout & benefits
• Goal is to create an updated framework for selling SaaS to Enterprise
customers and share this across the industry.
• Everyone who leaves a business card or contacts me on
Linkedin at then end of the session, will get a free copy of the
following:
• Framework selling SaaS to Enterprise customers including the
findings from this workshop
• Qualification checklists
• Proposal template(s)

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