What you'll get
- 6 copy-ready blocks
- 6 min read
- Two jobs, not one
- Score each H, O or N
- The total
- Fill in both columns
- If you hire
- If you outsource
How to use it
- Step 1: Split the job with Part 1 before you compare people or vendors.
- Step 2: Score the eight questions in Part 2 and total the letters.
- Step 3: Fill in the cost sum in Part 3 with your own figures.
- Step 4: Read the verdict in Part 4 and take the 90-day plan for your path.
A first sales hire at a startup usually goes wrong in one of two ways: the founder hires a closer when the company needs conversations, or outsources outreach nobody inside can feed or judge. This sheet splits the job, scores eight questions about your situation and prices both paths in your own figures.
Part 1: Split the job
Two jobs, not one
Job A Opening: lists, research, outreach, first conversations.
Job B Closing: demos, proposals, negotiation, signatures.
Who closes today: [name] (usually the founder, and for now it should stay there)
What you are short of: [conversations / signatures]If you are short of signatures, stop here: neither a hire nor a vendor fixes a close the founder has not cracked. This sheet decides Job A, the opening work, which is where most founders are short.
Part 2: The eight questions
Score each H, O or N
1. Have you sold this yourself, start to close, for six months or more?
H or O: yes N: no. Keep selling before you delegate anything.
2. Is your message settled, or still changing every month?
H: still moving, keep the learning close O: settled enough to brief a stranger
3. Can you give the work two or more hours a week of management?
H: yes, more O: barely two
4. Is your market a short list of named companies, or broad?
H: a short list that must be learnt deeply O: either, if the vendor works your approved list
5. Do you need the selling knowledge to stay in the company?
H: yes, this becomes a team O: not yet, we need conversations first
6. What can you fund?
H: a year of salary whatever happens O: a monthly engagement you can stop
7. Who will train and coach this person?
H: a founder who has sold O: nobody has the time; buy an existing process
8. When do you need conversations?
H: we can wait out a ramp of months O: this quarterThe total
Any N: not ready. Sell for another quarter, then score again.
Five or more H: hire. Take the hire plan in Part 4.
Five or more O: outsource. Take the vendor plan in Part 4.
Four and four: outsource short term while you prepare the hire. Revisit in a quarter.Part 3: The cost sum
No market figures here; salaries and engagement prices vary too much by city and market. Use the offer letters and quotes in front of you, and count your own hours, because they are the figure founders forget.
Fill in both columns
HIRE
Salary a year: [ ]
Incentive at plan: [ ]
Tools, data and phone a year: [ ]
Your coaching time, hours a week: [ ]
Months before a full week of work: [ ]
OUTSOURCE
Monthly engagement: [ ]
Minimum term, months: [ ]
Your review time, hours a week: [ ]
Weeks to first outreach: [ ]
Cost of the minimum term: [ ]Compare the cost of reaching one sustained month of real conversations on each path, not the monthly lines. A cheaper month with a longer ramp is often the dearer year. The SDR Cost Calculator runs this sum with your own figures.
Part 4: The first 90 days, either path
If you hire
Weeks 1 to 2 They shadow every call you take. Write down your message as you actually say it.
Weeks 3 to 4 They build the named list with you and research the first tier.
Weeks 5 to 8 They open accounts, with you reviewing every note before it sends.
Weeks 9 to 12 They run alone, you review weekly. Judge on accounts opened, not activity.If you outsource
Week 1 Vet before you sign: named people, data sources, a written definition of qualified.
Weeks 2 to 3 Approve the account list and the message. Nothing sends that you have not read.
Weeks 4 to 10 Weekly review on accounts and conversations, not sends and opens.
Weeks 11 to 12 Decide with evidence: extend, fix or exit on the terms you set.Vet the vendor with the Lead-Gen Agency Vetting Checklist and put the terms through the Outsourced SDR Contract Checklist before you sign.
Worked example (illustrative, not a real company)
Quaywise sells warehouse software. Its founder has sold alone for a year, closes most proposals that get written and is short of conversations, not signatures. Scoring the sheet: the message is settled, which points O, but the market is a short list of named logistics companies, the knowledge should stay in the company, there is time to coach, a year of salary is fundable and the ramp can be waited out. Six H against one O. Quaywise hires, and Sam Carter joins to open named accounts with the founder reviewing every note for the first eight weeks. All names and details are invented.
Five mistakes to avoid
- Hiring a closer to fix a pipeline problem. A great closer with no conversations is an expensive diary.
- Outsourcing a message that still changes weekly. You pay a vendor to learn something you have not settled.
- Comparing the salary with the monthly fee and ignoring your own hours. Both paths cost founder time; only the amount differs.
- Hiring for the logo on the CV. Someone who sold with a famous brand behind them has never sold without it.
- Treating the decision as permanent. With a term and an exit, outsourcing is reversible; with a fair ramp, so is a hire. Not ready is also an answer.
Why this works on named accounts
Common questions
When should a startup make its first sales hire?
After the founder has sold the product repeatedly and can write down who buys, why and what they say. A first hire inherits a process; they rarely invent one. If no deals have closed founder-led, the next seller is still the founder.
Should a startup's first sales hire be senior or junior?
Match the person to the job you scored. Opening work on named accounts suits a hungry mid-level person with a founder coaching. A senior closer only pays once conversations exist. The expensive mistake is a senior title doing junior work, or the reverse.
Is outsourcing sales a bad idea for a startup?
Not when it is scoped as opening, not closing. A vendor can research, reach out and start conversations on an account list you approve. Buyers want the founder in the room to close, so keep Job B at home either way.
More from the Academy
Outsourced SDR Contract Checklist
For founders and sales heads holding a proposal from an outsourced SDR or sales outsourcing provider.
You leave with a 30-point contract checklist, five clauses to ask for in writing and a sheet to compare three proposals.
Lead-Gen Agency Vetting Checklist
For founders and sales leads holding a lead generation proposal.
You leave with 12 questions to send in writing, the evidence to ask for with each, six walk-away signs and a sheet to file with the contract.
After Referrals Dry Up: A 30-Day Client Plan
For founders and sales heads of software and IT services companies whose referrals have slowed.
You leave with a named account list, a research card per Tier 1 account, a 30-day outreach plan and a weekly tracking sheet.
SDR Cost Calculator
Compare the cost of hiring an SDR in-house with an outsourced SDR and an AI SDR, on your own figures. Runs in your browser.
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