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Head of Customer Success, Fieldline

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Head_of_CS_Fieldline.pdf Read 1 page, 192 words
Your Job Description
Head of Customer Success Fieldline, Boston (hybrid) About Fieldline Fieldline builds scheduling and dispatch software for commercial HVAC and mechanical contractors. We're 28 people, Series A, and about 140 contractors run their day on us. The role You'll be our first customer success hire, reporting to our CEO. You'll own what happens after a contract is signed. What you'll bring - 6+ years in customer success or account management at a B2B SaaS company - 2+ years managing people - Experience selling to or working with trades, field service, or construction customers - Comfortable in the details of a messy implementation Nice to have - Experience at a company between 20 and 100 people - Familiarity with HubSpot or Vitally - Spanish How we work We pick up the phone. We show the work.

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Head of Customer Success, Fieldline

What your job description asks for

Background & experience

What the ideal candidate has done
  • Customer success or account management at B2B SaaS, 6+ years From your JD: “6+ years in customer success or account management at a B2B SaaS company”
  • Managing people, 2+ years From your JD: “2+ years managing people”
  • Worked with trades, field service, or construction customers From your JD: “Experience selling to or working with trades, field service, or construction customers”
  • Has run messy customer implementations From your JD: “Comfortable in the details of a messy implementation”
  • Worked at a 20–100 person company From your JD: “Experience at a company between 20 and 100 people”
  • Has used HubSpot or Vitally From your JD: “Familiarity with HubSpot or Vitally”
  • Has built a customer success function from zero ImpliedInferred from “our first customer success hire” and “set up health scoring, QBRs, and playbooks”
  • Has hired a team ImpliedInferred from “Hire and lead a team of 2–3 CSMs over the next 12 months”
Head of Customer Success, Fieldline
Background requirement 3 of 8
You asked for 6+ years in customer success at a B2B SaaS company. That’s usually shorthand for a few things. Which of these do you actually need?
Select all that apply
Triages a book of accountsLeads a renewal with an economic buyer
Got it: two skills added. Given those, does the background itself still matter?I’d suggest loosening it. The resume review still needs something to go on, but six years at a SaaS company isn’t the only way to get there.
Choose one
Loosen it
Here’s a broader version for the resume review. It keeps the signal without the six-year filter:
6+ years in customer success or account management at a B2B SaaS company
Has owned B2B customer accounts after the sale, with a renewal or retention outcome
Head of Customer Success, Fieldline
Comparison 2 of 6

Who’s the stronger candidate?

Two realistic mock candidates. Go with your gut; your choices show what you actually care about.

Candidate A

Background
7 years as a CSM at a B2B marketing software company
Customer accounts
Owned 40 accounts with renewal targets
Implementations
Handed off to a separate onboarding team
Managing people
Led 2 CSMs for a year
Industry
Marketing software

Candidate B

Background
Ran operations at an HVAC contractor, then 3 years leading implementations at a field service software company
Customer accounts
No renewal ownership
Implementations
Led 25+ rollouts to field teams
Managing people
Managed dispatchers and a scheduler
Industry
Trades and field service
Would you actually interview Candidate B?
You picked B, who has no B2B SaaS experience. What makes up for it?
Select all that apply
Your answer becomes a screening profile.
Head of Customer Success, Fieldline
Round 3 of 8

Of these four, which matters most for this role? Which matters least?

Most importantRequirementLeast important
Leads a renewal with an economic buyerTies value delivered to price; handles a price objection without discounting first.
Drives end-user adoptionGets field technicians, not just the buyer, using the product within 30 days.
Gives direct, specific feedbackRaises problems with a report within days, tied to specific behavior.
Builds what’s missingMakes the tool or process needed rather than waiting for one.
Head of Customer Success, Fieldline

Your hiring criteria

Everything you’ve refined and ranked, in one place. Your updated JD, resume review, and interview plan all come from this list. Posted criteria appear in the JD; evaluation only criteria shape the interview plan but aren’t shared publicly.

Ranked by your choices. Standards stay internal; the JD states the skill.
  1. 1 Drives end-user adoptionGets field technicians, not just the buyer, using the product within 30 days. Must-have
  2. 2 Leads a renewal with an economic buyerTies value delivered to price; handles a price objection without discounting first. Must-have
  3. 3 Runs a messy implementationScopes before committing to a date, plans the migration, re-plans in the open when it slips. Must-have
  4. 4 Gives direct, specific feedbackRaises problems with a report within days, tied to specific behavior. Must-have
  5. 5 Spots churn risk before renewalReads usage and support signals to flag at-risk accounts a quarter ahead. Must-have
  6. 6 Hires against clear criteriaDefines what good looks like for a role before recruiting, and decides against it. Must-have
  7. 7 Triages a book of accountsDecides which of 30+ accounts need attention this week from usage and relationship signals. Nice-to-have
  8. 8 Understands SaaS retention mechanicsExplains how churn, contraction, and expansion roll into net revenue retention. Nice-to-have
Head of Customer Success, Fieldline

Your revised job description

Original

What you’ll bring

  • 6+ years in customer success or account management at a B2B SaaS companyBroadened
  • 2+ years managing peopleBroadened
  • Experience selling to or working with trades, field service, or construction customersBroadened
  • Comfortable in the details of a messy implementationClarified

Nice to have

  • Experience at a company between 20 and 100 peopleRemoved
  • Familiarity with HubSpot or VitallyRemoved
  • SpanishUnchanged
About, responsibilities, location, and how we work are unchanged.
Revised New or rewritten

What you’ll bring

  • You get field teams using new software: you’ve led rollouts where technicians, not just the buyer, adopted the product.
  • You can lead a renewal with the person who signs, tying the value delivered to the price.
  • You can run a messy implementation: scope before committing to a date, plan the data migration, and re-plan in the open when it slips.
  • You give the people you lead direct, specific feedback.
  • You’ve owned B2B customer accounts after the sale, with a renewal or retention outcome, or you’ve run operations in a trades or field service business and led software rollouts to field teams.
  • You’ve led people or work through others.

Nice to have

  • Spanish

Pressure-test what you’re looking for

Job requirements are the foundation of any hiring plan. Winnow pulls every requirement from your JD, including what’s hiding, then helps you articulate what matters most.

Head of Customer Success, Fieldline

Your hiring plan.

Select your stages and confirm where and when you’ll assess each requirement.

Stages in your process
Stage 1

Resume review

  • Background Has owned B2B customer accounts after the sale, with a renewal or retention outcome Must-have
  • Background Ran operations in a trades or field service business, then led software rollouts to field teams Must-have
  • Background Has led people or work through others Must-have
Stage 2

Recruiter screen

  • Values & Approach Defaults to direct, real-time contact Must-have
  • Skill Spots churn risk before renewal Must-have
  • Logistics Works from Boston, hybrid Must-have
  • Skill Spanish Nice-to-have
Stage 3

Hiring manager interview

  • Skill Leads a renewal with an economic buyer Must-have
  • Skill Runs a messy implementation Must-have
  • Skill Hires against clear criteria Must-have
Stage 42

Team interviews

Interview 1
  • Skill Gives direct, specific feedback Must-have
  • Skill Drives end-user adoption Must-have
  • Skill Triages a book of accounts Nice-to-have
Interview 2
  • Values & Approach Shows their reasoning Nice-to-have
  • Skill Runs a messy implementation Must-have
  • Skill Spots churn risk before renewal Must-have
  • Drop here
Stage 5

Reference checks

  • Values & Approach Defaults to direct, real-time contact Must-have
  • Skill Drives end-user adoption Must-have
  • Skill Gives direct, specific feedback Must-have
  • Skill Hires against clear criteria Must-have
Head of Customer Success, Fieldline
Stage 1 of 5

Resume review

  1. At least one of
    • Has owned B2B customer accounts after the sale, with a renewal or retention outcome
      Counts: A CSM or account manager role with renewal or retention responsibility. Doesn’t count: Pre-sale roles only, like SDR or AE, with no post-sale ownership.
    • Ran operations in a trades or field service business, then led software rollouts to field teams
      Counts: An operations, dispatch, or service manager who led a software rollout. Doesn’t count: A field technician role without leading the rollout.
  2. Has led people or work through others
    Counts: Direct reports, or leading a project team or cross-functional rollout. Doesn’t count: Individual contributor work only.
Head of Customer Success, Fieldline
Stage 3 of 5

Hiring manager interview

This interview passes if

Every must-have averages 3 or higher, and no question scores a 1.

Leads a renewal with an economic buyer

Must-have
  1. Scorecard
    • 4Strong PassTies value delivered to price, with numbers, before any discount. Goes straight to the person who signs.
    • 3PassDefends value with specifics. Concedes something, but deliberately.
    • 2Partial PassGeneral value talk. Leads with a discount.
    • 1No PassNo real example, or blames the customer.

Runs a messy implementation

Must-have

Hires against clear criteria

Must-have

Map the process end-to-end

Winnow suggests where in the hiring process to assess each requirement, but you retain full control. Open any stage to build an interview or screening guide, complete with rubrics. Winnow shows you a first draft so you have something to react to.

Interview guide, stage 3 of 5

Hiring manager interview

Head of Customer Success, Fieldline
This interview passes if Every must-have averages 3 or higher, and no question scores a 1. Must-haves in this interview: leads a renewal with an economic buyer; runs a messy implementation; hires against clear criteria.

Leads a renewal with an economic buyer

1.Walk me through a renewal where the customer pushed back on price. What did you do?
4Strong PassTies value delivered to price, with numbers, before any discount. Goes straight to the person who signs.
3PassDefends value with specifics. Concedes something, but deliberately.
2Partial PassGeneral value talk. Leads with a discount.
1No PassNo real example, or blames the customer.
Notes
Score4321
2.Tell me about a renewal you lost. What would you do differently?
4Strong PassOwns the loss, names the earlier signal they missed, and says what they changed after.
3PassOwns the loss; the lesson is general.
2Partial PassPartly blames circumstances.
1No PassNo example, or blames the customer.
Notes
Score4321

Off you go!

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