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● Currently the CCO  Capdesk
● I’m Danish / Dutch / Caribbean
● Spent 10 years in UK Study / Work)
● 2 Degrees in Pharmaceuticals
● Was the first UK Sales hire for Pleo
● Try to keep my podcast alive aimed at employees
Stephen Allott, Venture Partner,
Seedcamp
Recommended reads written by Stephen:
● Sales tales: the first sales hire is the hardest
● Sales tales: you’re selling not buying, when
sales hiring
Link to all his Medium posts:
● https://stephenallott.medium.com/
Find him on Linkedin:
● https://www.linkedin.com/in/stephenaallott/
Advice from an expert
Seedcamp Sales Tales
“You’ve built your MVP, validated the market with “initial
customers that desperately need your product and are
paying for it”, the founders can sell but not experts
and not scalable”
“Best advice for your first hire?”
My Goal:
Help remove as much self doubt as possible
when hiring your first salesperson
Characteristics:
1. You currently do founder led-sales
2. Team size might be between 3 and 20ish
3. Limited or no inbound sales traction
4. You are a pre-seed & B2B SaaS business
5. Target customers are SMB to SME
(not enterprise level)
Image credit: https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d
Let's assume your company looks like this
Founder runs sales
Product Visionary attends
sales calls as a ‘pre-sales
engineer’ handling technical
queries if necessary
Founder sales mode
What an interim can do for your business
✅ Can hire reps who have raw potential
with expert guidance from coaching
✅ Can make sure you get the basics right,
things like CRM, scripts, deal stages etc
✅ Can source & assess talent far better
than you can
✅ Can accurately assess if it’s sales not
performing or product
✅ They can calm the nerves of sales, things
like “this is a normal feeling I’ve seen this
Before”
✅ It will help you avoid management/
leadership dept
Image credit: - https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d
Sifted article on Leadership Dept - https://sifted.eu/articles/leadership-debt/
Ideal advice: Hire an Interim to get you started
Founder
continues to
run sales, and
learns sales
management
Interim works with Founder:
● Specifies and recruits new reps
● Sets quotas and territories
● Designs comp plans
● On-boards new reps
● Coaches Founder on sales management
● E.g. on lead gen or closing plans
1 or 2 days per week
Sales Interim org setup
“I would assume 3.5 to 3.75K
DKK per 8 hours (day) of time
(roughly)” or you go equity
component if they believe
How to spot a potential interim? What to look for?
Challenges:
❓ It can take time to find this person
❓ How much time can they really commit?
❓ How do you know what good looks like?
Image credit: https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d
You want to get to this as fast as possible 👇🏻
Founder continues
as sales manager,
supported by
the interim
Interim works with Founder:
● Coaches Founder on sales
management
● Recruits new sales manager
and further reps
1 or 2 days per week
Founder with expert help hires first 2 sales reps
“But hey! We don’t live in the perfect world and for 99% of us
that option I shared won’t be easy to come by and you won’t
have the luxury of time, so what’s option two?”
“Best advice for your first hire - Take 2” 😉
- Founder led
- No PMF
- V.little money
- Lots of equity
- V. little FLS
- Solid PMF
- Plenty of money
- Scaling issues
- Less equity
“The sales profile you need today, will not be the one you need in a year or so, as you change as you
scale and it’s important to adapt to this change and be clear internally on why”
- Less Founder led
- Some PMF
- Some money
- Lots of equity
PS S A
- Pure Hunter
- Passion problem
solver
- Can just make things
happen
- Pure Hunter
- Passion problem
solver
- Need to see some
structure
- More sales specialisation
- Need lots of structure
- Can build and follow
process
Embrace one truth
1. What to look for in a first sales hire
(and maybe how to find them)
2. How to evaluate if they could be a good fit
(a strong framework)
3. How to help them have a fighting chance
& what to do if it doesn’t work out
(all breakups don’t have to be bad)
12
Examples of strong startup sales rep
What characteristics you should be looking for:
1. Attitude
a. Resilience - can handle rejection and or
welcomes it as feedback
b. Hunger - something to prove for
themselves
2. Coachability
a. Humble - no ego’s or sharp elbows just
wants to be the best
b. A Doer - puts things in motion less talking
3. Curiosity
a. Knowledge - seeks out learning from
everyone especially customers
b. Creativity - outside the box thinking what
else could we do
Why could these be good first sales hires? What to look for:
1. What to look for in a first sales hire
(and maybe how to find them)
2. How to evaluate if they could be a good fit
(a strong framework)
3. How to help them have a fighting chance
& what to do if it doesn’t work out
(all breakups don’t have to be bad)
Take as much guesswork out of assessing people while
giving them an interesting experience
1. Screening Stage
a. You’re looking to assess Attitude
i. Resilience & Hunger
2. Challenge Stage
a. You’re looking to assess Coachability
i. Competency for the role
ii. Flexibility to change quickly
3. Interviews Stage
a. You’re looking to assess Curiosity
i. Through the process have they
become more curious and seeking
more knowledge with questions
Some inspiration on process:
https://blog.capdesk.com/hakon-junge-how-we-hire
Set up a solid recruitment process & framework from day 1
Link to our challenges for inspiration: https://drive.google.com/drive/folders/134rDOWC6ltKc7E-nfBG1bCz7umCEDxPK?usp=sharing
How to assess a good first sales hire. What to look for using a challenge.
1. What to look for in a first sales hire
(and maybe how to find them)
2. How to evaluate if they could be a good fit
(a strong framework)
3. How to help them have a fighting chance
& what to do if it doesn’t work out
(all breakups don’t have to be bad)
18
1. Set reasonable expectations & iterate
A. Agree on a timeline (trial run) if you have to
B. Look at the leading indicators as much as the results
2. Respect it’s going to be a learning process
A. You need to sell with them
B. If revenue isn’t coming you need to drill into
why and the reps need to drive this process
C. Give them your time but set the tone they
need to ask for it
3. If after 3 months it’s clear things aren’t working
don’t be afraid to pull the plug
A. This is why probation periods exist
B. With weekly 1 on 1’s there shouldn’t be any
surprises both ways
Some simple high level thoughts here
Slides from PSV Academy StartupTalk #30 - Founder's Guide to the First Sales Hire ( 3 of 3)

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Slides from PSV Academy StartupTalk #30 - Founder's Guide to the First Sales Hire ( 3 of 3)

  • 1.
  • 2. ● Currently the CCO  Capdesk ● I’m Danish / Dutch / Caribbean ● Spent 10 years in UK Study / Work) ● 2 Degrees in Pharmaceuticals ● Was the first UK Sales hire for Pleo ● Try to keep my podcast alive aimed at employees
  • 3. Stephen Allott, Venture Partner, Seedcamp Recommended reads written by Stephen: ● Sales tales: the first sales hire is the hardest ● Sales tales: you’re selling not buying, when sales hiring Link to all his Medium posts: ● https://stephenallott.medium.com/ Find him on Linkedin: ● https://www.linkedin.com/in/stephenaallott/ Advice from an expert Seedcamp Sales Tales
  • 4. “You’ve built your MVP, validated the market with “initial customers that desperately need your product and are paying for it”, the founders can sell but not experts and not scalable” “Best advice for your first hire?” My Goal: Help remove as much self doubt as possible when hiring your first salesperson
  • 5. Characteristics: 1. You currently do founder led-sales 2. Team size might be between 3 and 20ish 3. Limited or no inbound sales traction 4. You are a pre-seed & B2B SaaS business 5. Target customers are SMB to SME (not enterprise level) Image credit: https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d Let's assume your company looks like this Founder runs sales Product Visionary attends sales calls as a ‘pre-sales engineer’ handling technical queries if necessary Founder sales mode
  • 6. What an interim can do for your business ✅ Can hire reps who have raw potential with expert guidance from coaching ✅ Can make sure you get the basics right, things like CRM, scripts, deal stages etc ✅ Can source & assess talent far better than you can ✅ Can accurately assess if it’s sales not performing or product ✅ They can calm the nerves of sales, things like “this is a normal feeling I’ve seen this Before” ✅ It will help you avoid management/ leadership dept Image credit: - https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d Sifted article on Leadership Dept - https://sifted.eu/articles/leadership-debt/ Ideal advice: Hire an Interim to get you started Founder continues to run sales, and learns sales management Interim works with Founder: ● Specifies and recruits new reps ● Sets quotas and territories ● Designs comp plans ● On-boards new reps ● Coaches Founder on sales management ● E.g. on lead gen or closing plans 1 or 2 days per week Sales Interim org setup
  • 7. “I would assume 3.5 to 3.75K DKK per 8 hours (day) of time (roughly)” or you go equity component if they believe How to spot a potential interim? What to look for?
  • 8. Challenges: ❓ It can take time to find this person ❓ How much time can they really commit? ❓ How do you know what good looks like? Image credit: https://stephenallott.medium.com/sales-tales-the-first-sales-hire-is-the-hardest-981d09a8f17d You want to get to this as fast as possible 👇🏻 Founder continues as sales manager, supported by the interim Interim works with Founder: ● Coaches Founder on sales management ● Recruits new sales manager and further reps 1 or 2 days per week Founder with expert help hires first 2 sales reps
  • 9. “But hey! We don’t live in the perfect world and for 99% of us that option I shared won’t be easy to come by and you won’t have the luxury of time, so what’s option two?” “Best advice for your first hire - Take 2” 😉
  • 10. - Founder led - No PMF - V.little money - Lots of equity - V. little FLS - Solid PMF - Plenty of money - Scaling issues - Less equity “The sales profile you need today, will not be the one you need in a year or so, as you change as you scale and it’s important to adapt to this change and be clear internally on why” - Less Founder led - Some PMF - Some money - Lots of equity PS S A - Pure Hunter - Passion problem solver - Can just make things happen - Pure Hunter - Passion problem solver - Need to see some structure - More sales specialisation - Need lots of structure - Can build and follow process Embrace one truth
  • 11. 1. What to look for in a first sales hire (and maybe how to find them) 2. How to evaluate if they could be a good fit (a strong framework) 3. How to help them have a fighting chance & what to do if it doesn’t work out (all breakups don’t have to be bad)
  • 12. 12 Examples of strong startup sales rep What characteristics you should be looking for: 1. Attitude a. Resilience - can handle rejection and or welcomes it as feedback b. Hunger - something to prove for themselves 2. Coachability a. Humble - no ego’s or sharp elbows just wants to be the best b. A Doer - puts things in motion less talking 3. Curiosity a. Knowledge - seeks out learning from everyone especially customers b. Creativity - outside the box thinking what else could we do
  • 13. Why could these be good first sales hires? What to look for:
  • 14. 1. What to look for in a first sales hire (and maybe how to find them) 2. How to evaluate if they could be a good fit (a strong framework) 3. How to help them have a fighting chance & what to do if it doesn’t work out (all breakups don’t have to be bad)
  • 15. Take as much guesswork out of assessing people while giving them an interesting experience 1. Screening Stage a. You’re looking to assess Attitude i. Resilience & Hunger 2. Challenge Stage a. You’re looking to assess Coachability i. Competency for the role ii. Flexibility to change quickly 3. Interviews Stage a. You’re looking to assess Curiosity i. Through the process have they become more curious and seeking more knowledge with questions Some inspiration on process: https://blog.capdesk.com/hakon-junge-how-we-hire Set up a solid recruitment process & framework from day 1
  • 16. Link to our challenges for inspiration: https://drive.google.com/drive/folders/134rDOWC6ltKc7E-nfBG1bCz7umCEDxPK?usp=sharing How to assess a good first sales hire. What to look for using a challenge.
  • 17. 1. What to look for in a first sales hire (and maybe how to find them) 2. How to evaluate if they could be a good fit (a strong framework) 3. How to help them have a fighting chance & what to do if it doesn’t work out (all breakups don’t have to be bad)
  • 18. 18 1. Set reasonable expectations & iterate A. Agree on a timeline (trial run) if you have to B. Look at the leading indicators as much as the results 2. Respect it’s going to be a learning process A. You need to sell with them B. If revenue isn’t coming you need to drill into why and the reps need to drive this process C. Give them your time but set the tone they need to ask for it 3. If after 3 months it’s clear things aren’t working don’t be afraid to pull the plug A. This is why probation periods exist B. With weekly 1 on 1’s there shouldn’t be any surprises both ways Some simple high level thoughts here