Mid-Market Sales Team readiness - Discovery Questionnaire

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Discovery Questionnaire
RANDALL ISAAC
Mid Market Sales Executive
How Ready Is Your Software Company
to Build a Mid Market Sales Model?

How to Use The Readiness Assessment
• STOP: If you have not yet reviewed the Mid Market Strategy slide
deck, please do so prior to going through this document. It is available on
my Linkedin profile page
• The sections are grouped by Sales Model area – Corporate Executive,
Sales, Pre Sales, Marketing, Operations, Enablement).
• Typically each section will have an internal owner (i.e., Executive Suite,
VP Sales, VP Marketing, VP Operations, Enablement Manager, etc..).
• To validate answers and also to ensure enough time is allocated to each
area, its best if the owners are interviewed individually.
• To validate answers when there is overlap in responsibility across the
areas, some questions are repeated.
• The Output of this assessment is a formal project plan.

Executive Sponsorship
Objective: Ensure broad based executive
sponsorship allowing time and resources for the
Mid Market team to incubate.
Rough timelines to get to the Scale stage;
• The Preparation Stage: TBD - subject to Product,
Marketing, Operations and Channel readiness.
• The Incubation Stage: 3-6 months to hire initial sales
people, 3 months for enablement, and 6 – 9 months to
achieve meaningful pipeline conversion.
What is the level of sponsorship and buy-in of all key
executives on this project – CEO, COO, CFO, VP Sales:
• What are each of their perceptions of the opportunities and
challenges in the Mid Market?
• What is their annual revenue expectation for the first two years? Is
it realistic given time to prepare, recruit, enable, and achieve
pipeline conversion? Do they have the patience to commit to this?
• What is the budget for year one – sales, presales, marketing,
enablement, channel? (Start with at least 4 sales reps during the
incubation stage. Less than 4 is not a large enough sample
because success or failure be attributable a strong or weak
performer.)

Product
Objective: Align the product team strategy with Mid Market the Pipeline growth objective
 Design a Mid Market offering that has a paired down feature list desired by mid sized companies at an affordable price point
(software, support and services) with a relatively short sales cycle and low/no implementation effort.
 Ideally there is a free version that provides true value to the market being served and prompts prospects to give you their contact
information. It should have an easy, clear upgrade path to a paid offering. This offering should have zero implementation costs.
Discovery Questions
• How much revenue is the product currently generating in the Mid Market?
If it is do you have performance metrics – average order value, total
weekly pipeline growth, sales cycle length, rolling 4 quarter conversion
ratio?
• What feedback are you getting from sales and customers about the Mid
Market offering? Do you need to make adjustments? What are the barriers
to make the adjustments and how fast can they be made?
• Is there potential for a “Freemium” product? What is it? Is it on the market
today – if not when can it be ready? If available now, how many leads per
week is it driving? What is the seed/harvest path?
• Who implements the product: partners or your own services team? If
partners, is there a certification program? What is the cost of
implementation? Can mid market companies afford it?

Product Marketing
Objective: Ensure support material is in place to drive pipeline growth and opportunity conversion.
Group companies by 3-5 revenue or
employee segments. What is the Total
Addressable Market per segment?
Who are the Mid Market
competitors? Stack rank them.
What are your product’s
competitive differentiators?
What is the rough market
segment? How many
companies are in it?
Which segments need to be
served by Field resources
vs. Inside? Why?
What is the ROI of your
competitive differentiators?
Do you have the following built: product demo
server, one page tear sheet, standard sales demo
ppt slides, reference stories?

Sales Model – Type of Model
Any one of a variety of Mid Market sales models may be appropriate for your company. The key question to answer is whether
some or all Mid Market companies will required onsite visits to advance sales cycles. And if they do will they be handled by Field
based Enterprise sales reps, Field based Mid Market sales reps or Inside based sales reps with a travel budget.
• Fully Empowered Model:
The Mid Market team owns the complete sales
cycle within a defined market segment.
Companies that require onsite visits are handled
either by Inside reps with a travel budget or by
segmenting larger Mid Market companies and
creating territories for field based Mid Market
reps. High potential Mid Market sales people will
want prove their skills by working in this model.
Therefore it will produce the best sales people.
It’s also the most cost effective model;
- Doesn’t require double comping
- Sales commissions are owed only to Mid
Market reps at their lower compensation
rates.
• Team Model:
Inside / Field based Mid Market reps work
together to drive sales cycles across the
entire market. Typically the Inside rep
focuses on prospecting, appointment
setting and closing smaller opportunities.
Is useful where the product is too
complex for outsourced appointment
setters to be effective. This model is
expensive as it requires double comping.
• Hybrid Model:
Inside sales team owns a set of smaller
accounts, and teams with Field sales in
larger accounts where they work the
smaller deals, or have assigned
responsibilities. Double comping can be
avoided by commissioning Inside rep on
smaller deals, and Field rep on the larger
ones. A bonus will likely be required to
incentivize the reps to work the overlap
areas of responsibility. This model is
complicated in that there will likely be a
negative incentive to grow opportunities.
Note that it can be extended to support
for the Enterprise sales team in large,
complicated accounts.

Sales Model – Market Segmentation
Objective: Clearly set out the Mid Market territory and the rules around potential overlap areas
Vague rules or confusion about account ownership (Enterprise, Mid Market, Inside, Field, Channel,
etc..) will cause conflict, team distraction, lackluster prospecting and top reps leaving the organization.
Expectations and rules of engagement on all accounts should be set out in advance in compensation
plans. Conflict needs to be resolved quickly, consistantly and fairly.
What is the delineation of the market segment vs. that of other sales divisions?
• Segment is delineated by revenue, employee count or industry. What is the delineation?
• How will parent/subsidiaries be handled? Public organizations and ‘Crown’ corporations? Private
Equity/Venture Capital firms?
• How will onsite customer meetings be handled? Travel budget for Mid Market reps is clean.
Leveraging Enterprise sales people will require double comping and may cause the Enterprise
team to lose focus on their accounts. Allocating Mid Market Field resources is also viable.
• What is the policy for grandfathering of existing opportunities as other sales teams pull out of the
Mid Market segment?
- Existing rep gets X% of the commission for Y quarters.
- Existing reps can only ‘Grandfather’ opportunities that are at Z sales stage at the time the
territories are live

Finance
Compensation range needs to be set at market level within the city where the team is based. Within the range each rep needs to be
evaluated on their level of development across technical, sales business acumen and presentation skills with compensation adjusted
accordingly. Ideally comp is tied to the Mid Market development plan with base salary bumps as reps progress through enablement levels.
Commission payout should be consistent and timely. Any delay or inconsistency in commission payouts will cause distraction slow
pipeline growth.
What are the first year annual compensation and quotas?
• Compensation is typically set at 50:50 split of base salary to commission.
• What is the ramp up time against quota? Eg; Q1: 0%, Q2: 25%. Q3: 50%, Q4 100%
• Commission should be paid as soon as possible after cash is received on closed opportunities
• Team quota should be set ground up rather than top down. A top-down approach calculates team
quota based on achieving a % of the Total Addressable market. This is not a true reflection of your
company’s ability to execute. Use the ground up approach. Start with the amount of revenue
currently being driven in the segment, add a realistic growth rate, then calculate the number of reps
needed to hit that number based on market sales rep quotas.
• Based on the above, how many sales reps will be recruited in year one?
• Will the reps be Inside and/or Field based? Office or Virtual? Why?
• Where will the office be located? Why? Have you considered Canada where resource dollars can be
significantly stretched?

Marketing
Objective: Ensure required resources are in place to provide Mid Market sales
people with warm contacts to speak with in support of the pipeline growth
objective
Leads should come from four sources; internal marketing, freemium product
downloads, sales rep cold calling, and partner co-marketing events.
Internal Marketing needs to supply a flow of warm contacts for the team to speak with.
Sales reps will be expected to ‘dig’ for opportunities from these contacts.
• Has a dedicated marketing resource been identified? Who is it? What is their
background?
• How many leads per week are generated in the Mid Market segment today? Stack
rank campaign types.
• What is the marketing plan and budget for year one – marketing campaign types,
launch dates, budget allocations, estimated leads?
• Are there any co-marketing opportunities with Channel partners? Which ones? What
is the co-branded value prop? What is the partner contribution?
• What is your lead / opportunity / close conversion ratio
• What is your cost / lead?
• Does the marketing budget and conversion ratios support the sales quota? If not
how will the gap be closed?

Channel
Objective: The Channel program should incentivize partners to drive incremental pipeline
growth.
The Channel Partner program needs to be in alignment with the Mid Market Direct team.
Although partners may be needed for product implementation support, the Mid Market sales
team is primarily interested in partners finding incremental revenue pipeline. So the Partner
model should be constructed in a way that rewards them for sourcing net new opportunities.
• Is a Channel team in place? What is the internal org chart?
• Who are the partners, what is their areas of expertise?
• Are internal Channel managers and their partners incentivized to find incremental pipeline?
- Implementation partners (VARs) and Volume Resellers*: Does the partner model
incentivize them to find incremental opportunities? i.e, partners who perform better in
sourcing pipeline achieve higher ‘precious metals’ tiers, given more sales
opportunities, sub contract implementation work, recognition at customer events, etc.
- OEM partners: Are contracts designed in a way that incentivizes their customers to
contact the sales team and upgrade?
- Strategic Alliance partners: Are they actively co-marketing with you?
• What is the compensation model for internal people on opportunities involving Channel
partners? Ie., commission splitting, double comp, revenue enabling?
*see speaker notes for definitions of Partner types

Operations
Objective: Provide solutions that enable Mid Market leaders to manage growth, conversion and cycle length of large
volume pipelines
Mid Market sales teams drive large volumes of moderately sales opportunities. It is not possible to manage their performance on a
simple spreadsheet. There needs to be a CRM solution in place, formal forecast definitions, and a reporting solution to manage
pipeline growth, sales cycle velocity and conversion rates.
CRM – has it been implemented?
Reporting - needs to be capable of tracking the following
(by team and sales rep);
• Weekly total rolling 4 quarter (R4Q) pipeline growth
• Quarterly R4Q total pipeline conversion ratio by team
and sales rep is the basic requirement for analytic
needs. Nice to have is pipeline conversion from multiple
stages (i.,e sales demo to close, or technical decision to
close, etc.) [*see speaker notes for further explanation]
• Sales cycle length
• Current quarter + 1 sales forecast – preferably with
status detail
• Average order value
Forecast Definitions
• Are they standardized, formally captured by code in the CRM?
Definitions include: Closed/Booked, Probable, Upside, and Pipeline.
Performance Indicators
• How much is known about metrics? Quarter on quarter revenue
growth, lead acquisition cost, weekly rolling 4 quarter (R4Q)
pipeline growth, R4Q Conversion ratio, sales cycle length in days.

Recruitment – Sales Reps
Objective: Build a pipeline of people ‘young’ in their sales career but with a burning desire to carve out a successful
career in software sales. Recruitment needs to find people on the upswing – not stale, career Mid Market sales people.
The team is a proving ground. It’s a place to develop skills that drive people to positions of greater responsibility. Team members
need to be on their way up. Avoid the temptation to recruit people with a long history on Mid Market teams and who may be stale
in the role.
The best people will not have a long track record on their resumes. So the recruitment team needs to find people with potential
and internal drive to develop themselves into top industry sales professionals. The best people are not the ones who have a long
history in Mid Market sales and no advancements, they are the ones who come from any industry but have the intelligence,
passionate desire to build an outstanding career in sales
• How many sales and presales reps, over what period of time, need to be hired? How many Inside and/or Field based?
• What is the ideal profile of your Mid Market sales recruits – is vertical or line of business experience necessary? Software
experience necessary? How much sales experience is required? Does your model call for Inside and/or Field sales reps?
• Do you have in internal referral program? How is it communicated?
• How will you find recruits – job boards, recruitment agency etc.
• How much budget has been allocated per hire for recruitment?
• What is the interview process to identify high potential sales people – initial interview, presentation, multiple touches, standard
questionnaire, etc.?
• What are the rules around internal transfers (bringing them onto and off the team). Amount of time in current role, required
communication with current manager, etc.

Recruitment – Team Leader
Objective: identify a mature, experienced, driven, inspirational mentor to build a world class Mid Market team
The ideal leader of the Mid Market sales team is a steadfast advocate of the mission to develop people into the finest sales professionals in
the industry. They need to have a passion and patience to develop people into top talent. The person needs to be a diplomatic but firm
campaigner with the leaders across other key departments such as Recruitment, Marketing, Operations, Product, Enablement, Finance and
corporate executive to allocate resources and align with the team mission.
And this person needs to stay true to the mission when its tough professionally. An example of this is when a senior high performing Mid
Market rep is up for a promotion to another team. This puts revenue production at risk. A great celebrates this event and holds it up to the
team as a confirmation of the mission. A great leader will have anticipated this an ensure a robust pipeline of developing reps ready to step
in to take up the slack
• Is there a sales leader in place? Does this person have experience with Mid Market / high volume sales models?
• Does this person only have experience with Inside sales or do they bring a mature experience set with partners, Field sales and
Customers.
• Does this person have true passion to develop sales people? Why? What drives this passion?
• Does this person have a mature and calm demeaner when faced with conflict? Eg; account or opportunity ownership with other teams?
• Can this person communicate effectively and diplomatically with other departments to secure needed resources?
• Will your team rally around this person, and create a positive culture dedicated to professional development and high levels of activity?

Enablement
Objectives: develop the finest sales professionals in the industry, and win the
competition for motivated sales people within the local geographic area
Mid Market teams hire junior to intermediate level sales people. There will need to
be an enablement plan across technology (both yours and competitor’s), sales skills,
business acumen and presentation skills. This plan needs to be best of breed so
that it not only efficiently produces highly qualified sales professionals, but is also
leveraged to build you company’s brand as the premier destination for people who
want to develop a successful career in sales. It helps to win the competition for
people with the highest potential in the city.
Ideally the enablement plan has tiered graduation levels with the final being
Enterprise team ready
• What is the enablement budget?
• Who are the resources and what is plan to deliver enablement to the team?
• What material is ready? What is missing? When will it be ready?
• Have you settled on a sales methodology – or at a minimum a sales discovery
process? What is it?
• Is competitor training available?
• Industry business value proposition?

Tech Support
Objective: ensure technical support is efficient enough to
eliminate support calls to sales people, and dries satisfaction
levels such that customer routinely agree to reference stories
Customer technical support can be a huge distraction for sales people.
When customers don’t get resolution from the support team they call
their sales rep. This distraction will negatively impact pipeline growth.
On the flip side, when tech support is delivered effectively and
customer are happy, they agree to do reference stories which helps to
drive sales conversion.
• How is Tech Support delivered? Online, live, etc..
• What is the cost of the packages for Mid Market customers? Is it
affordable?
• Is Support mandatory on all deals?
• What are the current challenges with Tech Support?
• Are there Mid Market customer references?

Sales Meetings - Cadence & Resourcing
Sales cadence is to validate forecast accuracy, and to surface constraints in
pipeline growth and conversion. Representatives of supporting departments
(Marketing, Operations, Enablement, Pre Sales) should attend to capture and
address action items relevant to their department.
What are the names, titles, and background of the representatives of relevant
departments required in the following meetings:
• Sales Forecast. Weekly. Items to review; current Quarter and Q+1. Attended by
sales leader, sales reps 1:1, presales and Mid Market sales operation manager.
• Marketing. Bi-weekly. Items to review: pipeline growth, marketing campaigns,
lead follow up and lead conversion. Attended by sales leader, sales team and
Mid Market marketing manager.
• Quarterly business review. Attended by sales team, operations, pre sales,
marketing. Items to review;
• Target accounts status;
• Q to date achievement, quota gap analysis, plan to close gap:
• Pipeline growth and conversion:
• Summary of items to achieve this quarter:
• Summary of items for management to resolve.

Team Culture
Objective: Create a high performing, activity-based culture whose
members enthusiastically live the team Primary Mission of continuous
professional development.
The team members will be highly driven to develop their career in sales, and
will maintain a high level of pipeline growth activity. At the same time they will
be under intense quota pressure. They will have an overriding mission of sales
excellence and pride in execution. If they are not excited, the first place it will
show up will be in the weekly pipeline growth numbers. An unhappy rep will not
prospect effectively.
So all efforts need to be made to use positive rather than negative
reinforcement. And the level of team excitement needs to be monitored. If it
looks like there is something adversely impacting the team, all efforts need to
be executed to find out what the issue is and how to quickly eliminate it.
Bottom line: the team must be excited, professional, and driven.

What Stage is Your Mid Market Model At?

What Stage Is Your Mid Market Model At?
Executive Sponsorship
• Broad executive support confirmed
Product Readiness
• Pricing, sizing & implementation model
finalized
• Seed / Harvest product is live
• Demo system in place
Marketing
• Budget for resources approved and is
justified by first year sales quota
Channel
• Partner model finalized and budgeted
Sales
• Coverage model finalized
• Recruitment budget approved
Sales Enablement
• Plan resourced, budgeted and
approved
Operations
• CRM and reporting solution in place
• Market Segmentation defined
Marketing
• Campaigns in full execution and
consistently producing weekly leads
Channel
• Partners recruited, BDM in place, and co-
branded marketing in execution
Sales Recruitment
• Sales people enabled, driving consistent
pipeline growth and closing opportunities
Sales Enablement
• Ongoing training being delivered
• Pieces of scalable model being built
Operations
• Confidence levels improving on Lead
acquisition cost and conversion, pipeline
growth potential by sales rep, R4Q
pipeline conversion ratios and sales cycle
length
Quarterly Revenue
• Team revenue growth beginning to
become consistent
IncubatePrepare
Marketing
• Significant weekly lead flow both from
internal marketing campaigns and sales
calls
• Multiple customer references available
Channel
• Partners consistently producing
incremental pipeline
Sales Recruitment
• Broad internal sponsorship to
aggressively expand team
Sales Enablement
• Scalable plan fully in place
• Brand as the destination to develop
sales skills is high in geographic region
Operations
• High confidence in all KPI and
conversion ratios
Quarterly Revenue
• Highly consistent and predictable
quarterly growth rates
Scale
Avoid hiring the sales team while in the Prepare stage….you aren’t ready for that expense

THANK YOU
604.360.1527 randalljisaac@gmail.com randall.isaac@sap.com RandallIsaac linkedin.com/in/randalljisaacRANDALL ISAAC

Appendix

Sample Revenue Growth
- MM compared with LE
Large Enterprise sales team
Quarter on quarter revenue can be bumpy
• Their quarterly performance is dependent on a defined set of
large deals.
• If any of their deals push, it has a significant effect on the
quarter’s revenue production
Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
Sample Comparative Revenue Performance
Mid Market: Large Enterprise
Mid Market
team revenue
Large Enterprise team
revenue
Mid Market sales team
Quarter on quarter revenue should provide a consistent
revenue foundation
• Their quarterly performance is based on a volume of average size
deals.
• No single deal should effect their quarter performance
• A fully operational system should provide a consistent flow of
growing revenue

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