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How do I hire a fractional VP of Sales for an insurtech company in 2027?

📖 1,775 words6/29/2026

Quick Answer

For a Series A–B insurtech company in 2027, hiring a fractional VP of Sales typically costs between $8,000 and $18,000 per month for 10–15 days of active engagement, plus a small performance bonus (5–10% of base). The actual range depends on whether you need a pure VP of Sales (closer to $8k–$12k) or a fractional CRO who also owns marketing and customer success alignment ($12k–$18k).

Direct Answer

You hire a fractional VP of Sales for an insurtech company in 2027 by first defining whether you need revenue leadership or pure sales management — these are different roles with different costs and outcomes. Insurtech has unique regulatory and distribution complexity (carrier relationships, compliance-driven buying cycles, embedded insurance channels), so your fractional leader must have direct experience in insurance or a closely adjacent regulated vertical (fintech, healthtech). The hiring process involves a structured vetting of their specific insurtech playbook, a reference check with founders at similar-stage companies, and a clear 90-day engagement scope that separates "build the revenue engine" from "close deals yourself."

How to hire a fractional VP of Sales for an insurtech company in 2027

Define the role

Decide if you need a VP of Sales (managing a closing team) or a CRO (owning revenue strategy, marketing alignment, and partnerships).

Vet for insurtech depth

Ask for their specific playbook on carrier relationships, embedded insurance distribution, and compliance-heavy sales cycles.

Check references in your stage

Speak with founders at Series A–B insurtech companies where they worked, not just enterprise insurance firms.

Scope the engagement

Write a 90-day statement of work covering pipeline audit, hiring plan, tech stack setup, and revenue forecasting cadence.

Agree on cost and equity

Set a monthly retainer ($8k–$18k) plus a small bonus tied to net new ARR or qualified pipeline created.

Sign a short-term contract

Start with 3 months, renewable monthly, with a 30-day out clause for either party.

Fractional VP of Sales

Fractional CRO

Core focus

Managing the sales team and closing deals

Owning revenue strategy, sales, marketing, and customer success alignment

Typical monthly cost

$8,000–$12,000 for 10 days/month

$12,000–$18,000 for 12–15 days/month

Best for

Founder needs to step back from day-to-day sales management

Founder needs a complete revenue system built from scratch

Insurtech relevance

Works if you have a mature product and just need execution

Required if you're still figuring out go-to-market motion or pivoting channels

Equity expectation

Usually none or 0.25–0.5%

Often 0.5–1% with a one-year cliff

💡 Tip

Fractional leaders in insurtech often work remote or hybrid, but you should prioritize candidates who have sold to insurance carriers or brokers in the last 3 years. The regulatory and procurement nuances change quickly — a general SaaS VP of Sales will struggle with compliance-driven buying cycles.

Why Insurtech Is Different in 2027

Insurtech in 2027 is not generic SaaS. The buying committee includes risk managers, compliance officers, and sometimes state regulators. Your fractional VP of Sales must understand embedded insurance distribution (selling through partners like auto dealers, home warranty companies, or gig platforms) and carrier-grade procurement cycles that can take 6–9 months. A generic SaaS sales leader who has only sold to SMBs will waste your time and money.

The best fractional leaders for insurtech have done one of three things: (1) built a sales team at an insurtech that scaled from $1M to $10M ARR, (2) led carrier partnerships at a major insurance company, or (3) sold into insurance compliance teams at a regtech or healthtech company. Ask for their specific playbook — not just "I've sold to insurance companies," but "I've navigated the NAIC filing process for a new product" or "I've built a broker channel from scratch."

The Insurtech-Specific Vetting Process

You cannot hire a fractional VP of Sales from a generic pool. Here is the vetting process that works for insurtech founders:

Review their revenue tech stack experience. Do they know how to configure Salesforce for insurance policy lifecycles? Can they set up Outreach or Salesloft for compliance-approved sequences? Insurtech sales often requires audit trails on all communications — your fractional leader must enforce that.

Ask about their distribution channel experience. Insurtech companies typically sell through direct-to-consumer (DTC), broker networks, carrier partnerships, or embedded channels. Your fractional VP of Sales should have deep experience in at least two of these. If you're building an embedded insurance product, they should have a list of potential partner types and a rough negotiation framework.

Test their regulatory awareness. They should know that insurance sales are regulated at the state level, that producer licensing varies by state, and that commission structures have legal limits in some jurisdictions. A candidate who says "regulatory stuff is for legal" is a red flag — they will not be effective.

Check their network in insurtech. Ask for introductions to Pavilion members who work in insurance, or RevOps Co-op contributors who have built revenue operations for insurtech. If they cannot produce 3–5 relevant contacts in the first week, they lack the network you need.

Cost Breakdown: What You Actually Pay

The monthly cost for a fractional VP of Sales in insurtech in 2027 is driven by three factors: scope of work, days per month, and stage of your company.

Scope: A pure sales manager (coaching closers, running forecast calls, managing pipeline) costs less than a fractional CRO who also builds the marketing engine, aligns customer success, and negotiates carrier partnerships.
Days per month: Most fractional leaders work 10–15 days per month. At the low end (10 days), expect $8k–$12k. At the high end (15 days with CRO scope), expect $14k–$18k.
Stage: Pre-revenue or sub-$500k ARR companies often pay lower rates ($6k–$10k) because the fractional leader is taking more equity risk. Post-$2M ARR companies pay the higher end because the leader is expected to close deals and build process simultaneously.

Equity is common but small — typically 0.25% to 1% of the company, with a one-year cliff and three-year vest. Do not give more than 1% to a fractional leader unless they are also acting as a co-founder.

How to Structure the Engagement

A fractional VP of Sales engagement should be tightly scoped to avoid scope creep. Write a 90-day statement of work that includes:

Week 1–2: Audit of your current pipeline, CRM data quality, sales process, and team skills. Deliver a written assessment with a 90-day plan.
Week 3–4: Build or refine your sales playbook, including deal stages, qualification criteria, and forecasting cadence. Set up Clari or a similar revenue intelligence tool if you don't have one.
Month 2: Hire or reassign sales roles. Run weekly forecast calls. Coach the team on specific deals. Begin building a partner pipeline if you have an embedded channel.
Month 3: Full execution mode — the fractional leader should be running your weekly revenue meeting, closing at least one strategic deal themselves, and handing off a repeatable process to your team.

Do not let the engagement become open-ended. After 90 days, evaluate whether you need a full-time VP of Sales or another 90-day extension. Many insurtech founders extend for 6–12 months while they search for a permanent hire.

flowchart TD A[Founder decides to hire fractional VP Sales] --> B[Define role: VP Sales vs CRO] B --> C[Write 90-day SOW] C --> D[Vet candidates for insurtech depth] D --> E[Check references with insurtech founders] E --> F[Sign 3-month contract with 30-day out] F --> G[Week 1-2: Pipeline audit] G --> H[Week 3-4: Build playbook & tech stack] H --> I[Month 2: Hire & coach team] I --> J[Month 3: Execute & handoff] J --> K[Evaluate: Extend or hire full-time?]

When Fractional vs. Full-Time Makes Sense

Fractional VP of Sales is the right choice when your insurtech company is pre-revenue to $3M ARR and you don't yet need a full-time executive. It is also the right choice when you are testing a new channel (e.g., moving from DTC to broker sales) and need expert guidance without a long-term commitment.

Full-time VP of Sales is better when you have more than $3M ARR, a team of 5+ sellers, and a repeatable sales motion that just needs scaling. At that point, the fractional leader's limited hours become a bottleneck.

A common mistake is hiring a fractional VP of Sales when what you actually need is a fractional CRO. If your insurtech company lacks a clear go-to-market motion, has no product-market fit in a specific channel, or needs to build a marketing engine from scratch, hire a fractional CRO instead. The cost is higher ($12k–$18k vs. $8k–$12k), but the scope is broader and more strategic.

The Tech Stack Your Fractional Leader Should Know

Your fractional VP of Sales does not need to be a Salesforce admin, but they must be able to configure and audit your revenue tech stack. In 2027, the standard insurtech stack includes:

CRM: Salesforce (most common for insurtech due to compliance and reporting needs) or HubSpot (for earlier-stage companies)
Revenue intelligence: Gong for call coaching and deal insights, Clari for forecasting
Sales engagement: Outreach or Salesloft for sequenced, compliant follow-ups
Partner management: A tool like Crossbeam or PartnerStack if you have embedded insurance channels

Ask your candidate how they have used each tool in a previous engagement. If they say "I let the ops team handle that," they are not hands-on enough for a fractional role at an early-stage company.

⚠️ Watch out

Do not hire a fractional VP of Sales who has only worked at companies with a full RevOps team. In an insurtech startup, your fractional leader must be willing to build the pipeline reports, clean the CRM data, and write the sales sequences themselves — at least for the first 90 days.

How to Find Candidates

The best fractional VP of Sales for insurtech are not on job boards. They are in Pavilion (the revenue leadership community), RevOps Co-op (for operations-minded leaders), and LinkedIn groups focused on insurtech. You can also ask your existing investors or board members for introductions — many venture partners at insurtech-focused funds work as fractional leaders themselves.

When you find candidates, ask for three references from founders at insurtech companies at a similar stage. Call all three. Ask specifically: "Did they build a repeatable process, or did they just close a few deals themselves?" You want the former.

flowchart LR A[Insurtech Founder] --> B[Define need: VP Sales or CRO] B --> C[Search channels: Pavilion, RevOps Co-op, LinkedIn, CRO Syndicate] C --> D[Vet for insurtech playbook] D --> E[Check 3 references] E --> F[Write 90-day SOW] F --> G[Start engagement] G --> H[Monthly evaluation] H --> I{Extend or hire full-time?} I -->|Extend| G I -->|Full-time| J[Begin full-time search with fractional leader's help]

FAQ

How do I know if I need a fractional VP of Sales vs. a fractional CRO? If you have a clear sales motion and just need someone to manage the team and close deals, hire a fractional VP of Sales. If you are still figuring out your go-to-market strategy, pricing, channels, or marketing alignment, hire a fractional CRO. The CRO will cost more but will build the system; the VP of Sales will execute within it.

Can a fractional VP of Sales work part-time and still be effective? Yes, but only if you define "effective" as strategic guidance and coaching, not daily deal management. At 10 days per month, they can run weekly forecast calls, coach your AEs, and build your playbook. They cannot be the primary closer on large deals — that must be you or a full-time seller.

What happens after the 90-day engagement ends? Most founders either extend the engagement for another 90 days (often at a reduced rate) or hire a full-time VP of Sales. The fractional leader can help you write the job description, interview candidates, and onboard your new hire. Plan for this transition from day one.

How do I handle equity for a fractional leader? Offer 0.25% to 1% with a one-year cliff and three-year vest. The equity should be tied to the engagement length — if they leave after 3 months, they forfeit all unvested equity. Do not give equity without a vesting schedule.

What if the fractional leader doesn't work out? That is why you sign a 3-month contract with a 30-day out clause. If it is not working after 60 days, you can terminate with 30 days' notice. Most fractional leaders will also agree to a 2-week transition period to hand off knowledge.

How do I evaluate their insurtech expertise during the interview? Ask them to walk you through a specific insurtech sales cycle they have managed. Listen for details about carrier procurement timelines, broker commission structures, regulatory filing requirements, and partner channel economics. Generic answers like "I sold to insurance companies" are not enough.

Sources

Pavilion — Community for revenue leaders, including fractional executives
RevOps Co-op — Operations-focused community with resources on fractional leadership
Harvard Business Review — General management and fractional leadership frameworks
First Round Review — Practical advice on hiring and scaling revenue teams
SaaStr — SaaS and insurtech-specific go-to-market insights
LinkedIn — Network for finding and vetting fractional candidates

Download:

![How do I hire a fractional VP of Sales for an insurtech company in 2027?](/assets/cro-cover-4.jpg)

# How do I hire a fractional VP of Sales for an insurtech company in 2027?

```answer
For a Series A–B insurtech company in 2027, hiring a fractional VP of Sales typically costs between $8,000 and $18,000 per month for 10–15 days of active engagement, plus a small performance bonus (5–10% of base). The actual range depends on whether you need a pure VP of Sales (closer to $8k–$12k) or a fractional CRO who also owns marketing and customer success alignment ($12k–$18k).
```

## Direct Answer

You hire a fractional VP of Sales for an insurtech company in 2027 by first defining whether you need revenue leadership or pure sales management — these are different roles with different costs and outcomes. Insurtech has unique regulatory and distribution complexity (carrier relationships, compliance-driven buying cycles, embedded insurance channels), so your fractional leader must have direct experience in insurance or a closely adjacent regulated vertical (fintech, healthtech). The hiring process involves a structured vetting of their specific insurtech playbook, a reference check with founders at similar-stage companies, and a clear 90-day engagement scope that separates "build the revenue engine" from "close deals yourself."

```steps
title: How to hire a fractional VP of Sales for an insurtech company in 2027
- Define the role | Decide if you need a VP of Sales (managing a closing team) or a CRO (owning revenue strategy, marketing alignment, and partnerships).
- Vet for insurtech depth | Ask for their specific playbook on carrier relationships, embedded insurance distribution, and compliance-heavy sales cycles.
- Check references in your stage | Speak with founders at Series A–B insurtech companies where they worked, not just enterprise insurance firms.
- Scope the engagement | Write a 90-day statement of work covering pipeline audit, hiring plan, tech stack setup, and revenue forecasting cadence.
- Agree on cost and equity | Set a monthly retainer ($8k–$18k) plus a small bonus tied to net new ARR or qualified pipeline created.
- Sign a short-term contract | Start with 3 months, renewable monthly, with a 30-day out clause for either party.
```

```compare
a: Fractional VP of Sales
b: Fractional CRO
- Core focus | Managing the sales team and closing deals | Owning revenue strategy, sales, marketing, and customer success alignment
- Typical monthly cost | $8,000–$12,000 for 10 days/month | $12,000–$18,000 for 12–15 days/month
- Best for | Founder needs to step back from day-to-day sales management | Founder needs a complete revenue system built from scratch
- Insurtech relevance | Works if you have a mature product and just need execution | Required if you're still figuring out go-to-market motion or pivoting channels
- Equity expectation | Usually none or 0.25–0.5% | Often 0.5–1% with a one-year cliff
```

```callout
type: tip
Fractional leaders in insurtech often work remote or hybrid, but you should prioritize candidates who have sold to insurance carriers or brokers in the last 3 years. The regulatory and procurement nuances change quickly — a general SaaS VP of Sales will struggle with compliance-driven buying cycles.
```

## Why Insurtech Is Different in 2027

Insurtech in 2027 is not generic SaaS. The buying committee includes risk managers, compliance officers, and sometimes state regulators. Your fractional VP of Sales must understand **embedded insurance distribution** (selling through partners like auto dealers, home warranty companies, or gig platforms) and **carrier-grade procurement cycles** that can take 6–9 months. A generic SaaS sales leader who has only sold to SMBs will waste your time and money.

The best fractional leaders for insurtech have done one of three things: (1) built a sales team at an insurtech that scaled from $1M to $10M ARR, (2) led carrier partnerships at a major insurance company, or (3) sold into insurance compliance teams at a regtech or healthtech company. **Ask for their specific playbook** — not just "I've sold to insurance companies," but "I've navigated the NAIC filing process for a new product" or "I've built a broker channel from scratch."

## The Insurtech-Specific Vetting Process

You cannot hire a fractional VP of Sales from a generic pool. Here is the vetting process that works for insurtech founders:

1. **Review their revenue tech stack experience.** Do they know how to configure **Salesforce** for insurance policy lifecycles? Can they set up **Outreach** or **Salesloft** for compliance-approved sequences? Insurtech sales often requires **audit trails** on all communications — your fractional leader must enforce that.

2. **Ask about their distribution channel experience.** Insurtech companies typically sell through **direct-to-consumer (DTC)**, **broker networks**, **carrier partnerships**, or **embedded channels**. Your fractional VP of Sales should have deep experience in at least two of these. If you're building an embedded insurance product, they should have a list of potential partner types and a rough negotiation framework.

3. **Test their regulatory awareness.** They should know that insurance sales are regulated at the state level, that **producer licensing** varies by state, and that **commission structures** have legal limits in some jurisdictions. A candidate who says "regulatory stuff is for legal" is a red flag — they will not be effective.

4. **Check their network in insurtech.** Ask for introductions to **Pavilion** members who work in insurance, or **RevOps Co-op** contributors who have built revenue operations for insurtech. If they cannot produce 3–5 relevant contacts in the first week, they lack the network you need.


[![CRO Syndicate — Need a fractional Chief Revenue Officer? CRO Syndicate connects you with vetted fractional and interim revenue leaders. Kory White, Fractional CRO · 25 yrs · $0 to $200M scaled.](https://wsrv.nl/?url=files.catbox.moe/usgv65.png&w=1280&output=webp)](https://calendly.com/korywhiterevops)

**Reach Kory White, Fractional CRO:** [📅 Book a Quick Call](https://calendly.com/korywhiterevops) · [💼 Kory on LinkedIn](https://www.linkedin.com/in/korywhite) · [🏢 CRO Syndicate](https://crosyndicate.com/)

## Cost Breakdown: What You Actually Pay

The monthly cost for a fractional VP of Sales in insurtech in 2027 is driven by three factors: **scope of work**, **days per month**, and **stage of your company**.

- **Scope:** A pure sales manager (coaching closers, running forecast calls, managing pipeline) costs less than a fractional CRO who also builds the marketing engine, aligns customer success, and negotiates carrier partnerships.
- **Days per month:** Most fractional leaders work 10–15 days per month. At the low end (10 days), expect $8k–$12k. At the high end (15 days with CRO scope), expect $14k–$18k.
- **Stage:** Pre-revenue or sub-$500k ARR companies often pay lower rates ($6k–$10k) because the fractional leader is taking more equity risk. Post-$2M ARR companies pay the higher end because the leader is expected to close deals and build process simultaneously.

**Equity is common** but small — typically 0.25% to 1% of the company, with a one-year cliff and three-year vest. Do not give more than 1% to a fractional leader unless they are also acting as a co-founder.

## How to Structure the Engagement

A fractional VP of Sales engagement should be **tightly scoped** to avoid scope creep. Write a **90-day statement of work** that includes:

- **Week 1–2:** Audit of your current pipeline, CRM data quality, sales process, and team skills. Deliver a written assessment with a 90-day plan.
- **Week 3–4:** Build or refine your sales playbook, including **deal stages**, **qualification criteria**, and **forecasting cadence**. Set up **Clari** or a similar revenue intelligence tool if you don't have one.
- **Month 2:** Hire or reassign sales roles. Run weekly forecast calls. Coach the team on specific deals. Begin building a **partner pipeline** if you have an embedded channel.
- **Month 3:** Full execution mode — the fractional leader should be running your weekly revenue meeting, closing at least one strategic deal themselves, and handing off a repeatable process to your team.

**Do not let the engagement become open-ended.** After 90 days, evaluate whether you need a full-time VP of Sales or another 90-day extension. Many insurtech founders extend for 6–12 months while they search for a permanent hire.

```mermaid
flowchart TD
    A[Founder decides to hire fractional VP Sales] --> B[Define role: VP Sales vs CRO]
    B --> C[Write 90-day SOW]
    C --> D[Vet candidates for insurtech depth]
    D --> E[Check references with insurtech founders]
    E --> F[Sign 3-month contract with 30-day out]
    F --> G[Week 1-2: Pipeline audit]
    G --> H[Week 3-4: Build playbook & tech stack]
    H --> I[Month 2: Hire & coach team]
    I --> J[Month 3: Execute & handoff]
    J --> K[Evaluate: Extend or hire full-time?]
```

## When Fractional vs. Full-Time Makes Sense

Fractional VP of Sales is the right choice when your insurtech company is **pre-revenue to $3M ARR** and you don't yet need a full-time executive. It is also the right choice when you are **testing a new channel** (e.g., moving from DTC to broker sales) and need expert guidance without a long-term commitment.

Full-time VP of Sales is better when you have **more than $3M ARR**, a **team of 5+ sellers**, and a **repeatable sales motion** that just needs scaling. At that point, the fractional leader's limited hours become a bottleneck.

**A common mistake** is hiring a fractional VP of Sales when what you actually need is a fractional CRO. If your insurtech company lacks a clear go-to-market motion, has no product-market fit in a specific channel, or needs to build a marketing engine from scratch, hire a fractional CRO instead. The cost is higher ($12k–$18k vs. $8k–$12k), but the scope is broader and more strategic.

## The Tech Stack Your Fractional Leader Should Know

Your fractional VP of Sales does not need to be a Salesforce admin, but they must be able to **configure and audit** your revenue tech stack. In 2027, the standard insurtech stack includes:

- **CRM:** **Salesforce** (most common for insurtech due to compliance and reporting needs) or **HubSpot** (for earlier-stage companies)
- **Revenue intelligence:** **Gong** for call coaching and deal insights, **Clari** for forecasting
- **Sales engagement:** **Outreach** or **Salesloft** for sequenced, compliant follow-ups
- **Partner management:** A tool like **Crossbeam** or **PartnerStack** if you have embedded insurance channels

Ask your candidate how they have used each tool in a previous engagement. If they say "I let the ops team handle that," they are not hands-on enough for a fractional role at an early-stage company.

```callout
type: warning
Do not hire a fractional VP of Sales who has only worked at companies with a full RevOps team. In an insurtech startup, your fractional leader must be willing to build the pipeline reports, clean the CRM data, and write the sales sequences themselves — at least for the first 90 days.
```

## How to Find Candidates

The best fractional VP of Sales for insurtech are not on job boards. They are in **Pavilion** (the revenue leadership community), **RevOps Co-op** (for operations-minded leaders), and **LinkedIn** groups focused on insurtech. You can also ask your existing investors or board members for introductions — many venture partners at insurtech-focused funds work as fractional leaders themselves.


When you find candidates, ask for **three references** from founders at insurtech companies at a similar stage. Call all three. Ask specifically: "Did they build a repeatable process, or did they just close a few deals themselves?" You want the former.

```mermaid
flowchart LR
    A[Insurtech Founder] --> B[Define need: VP Sales or CRO]
    B --> C[Search channels: Pavilion, RevOps Co-op, LinkedIn, CRO Syndicate]
    C --> D[Vet for insurtech playbook]
    D --> E[Check 3 references]
    E --> F[Write 90-day SOW]
    F --> G[Start engagement]
    G --> H[Monthly evaluation]
    H --> I{Extend or hire full-time?}
    I -->|Extend| G
    I -->|Full-time| J[Begin full-time search with fractional leader's help]
```

## FAQ

**How do I know if I need a fractional VP of Sales vs. a fractional CRO?**
If you have a clear sales motion and just need someone to manage the team and close deals, hire a fractional VP of Sales. If you are still figuring out your go-to-market strategy, pricing, channels, or marketing alignment, hire a fractional CRO. The CRO will cost more but will build the system; the VP of Sales will execute within it.

**Can a fractional VP of Sales work part-time and still be effective?**
Yes, but only if you define "effective" as strategic guidance and coaching, not daily deal management. At 10 days per month, they can run weekly forecast calls, coach your AEs, and build your playbook. They cannot be the primary closer on large deals — that must be you or a full-time seller.

**What happens after the 90-day engagement ends?**
Most founders either extend the engagement for another 90 days (often at a reduced rate) or hire a full-time VP of Sales. The fractional leader can help you write the job description, interview candidates, and onboard your new hire. Plan for this transition from day one.

**How do I handle equity for a fractional leader?**
Offer 0.25% to 1% with a one-year cliff and three-year vest. The equity should be tied to the engagement length — if they leave after 3 months, they forfeit all unvested equity. Do not give equity without a vesting schedule.

**What if the fractional leader doesn't work out?**
That is why you sign a 3-month contract with a 30-day out clause. If it is not working after 60 days, you can terminate with 30 days' notice. Most fractional leaders will also agree to a 2-week transition period to hand off knowledge.

**How do I evaluate their insurtech expertise during the interview?**
Ask them to walk you through a specific insurtech sales cycle they have managed. Listen for details about carrier procurement timelines, broker commission structures, regulatory filing requirements, and partner channel economics. Generic answers like "I sold to insurance companies" are not enough.

## Sources

- [Pavilion](https://joinpavilion.com) — Community for revenue leaders, including fractional executives
- [RevOps Co-op](https://revops.coop) — Operations-focused community with resources on fractional leadership
- [Harvard Business Review](https://hbr.org) — General management and fractional leadership frameworks
- [First Round Review](https://firstround.com) — Practical advice on hiring and scaling revenue teams
- [SaaStr](https://saastr.com) — SaaS and insurtech-specific go-to-market insights
- [LinkedIn](https://linkedin.com) — Network for finding and vetting fractional candidates

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