Full-Time

Head of Customer Success

Posted on 11/7/2025

Siteline

Siteline

11-50 employees

Subcontractor construction billing and AR platform

Compensation Overview

$140k - $172k/yr

+ Bonus

Remote in USA + 1 more

More locations: San Francisco, CA, USA

Hybrid

Category
Sales & Account Management
Required Skills
Sales
Marketing
Data Analysis
Requirements
  • 6+ years in customer success with 4+ years managing customer-facing teams in a SaaS environment and mid-market sales cycle
  • Experience with 0 to 1 building and scaling customer success operations with a focus on customer accountability and delivering value
  • Strong operations leader who is process and product savvy
  • Strong people and performance management skills
  • Analytical and process-oriented mind with the ability to think strategically along with willingness to execute and build from the ground up with a “no task too small” mindset
  • Excellent written and verbal communication skills. Demonstrated ability to present to diverse audiences and effectively communicate with internal stakeholders and customers
  • Customer-facing experience with a product that serves industries that are slow to adopt new technology is strongly preferred
Responsibilities
  • Manage the Customer Success team as they engage with customers, build relationships, drive adoption, and manage renewals
  • Responsible for coaching a high-performing team of Account Managers, Onboarding Managers, and Support/Integration Specialists
  • Own the entire post-sale customer lifecycle including onboarding, adoption, support and technical ticketing, and retention
  • Develop strategy, process improvements, and tooling for continued growth and efficiency
  • Develop and measure key team success metrics including adoption and engagement goals and report regularly to leadership
  • Collaborate with cross-functional teams including Product, Sales, Marketing, and Engineering to ensure that the voice of the customer is represented in strategic decisions
Desired Qualifications
  • Customer-facing experience with a product that serves industries that are slow to adopt new technology is strongly preferred
  • Familiar with Intercom, Salesforce, and Notion
  • Hybrid or Remote Office Environment: We value "working smart." This role is either based in our San Francisco office 3 to 4 days per week, with the option to work remotely on other days, OR fully remote (if based outside San Francisco).
  • Health & Wellness Benefits: Comprehensive health, dental, and vision insurance to support your well-being, along with wellness resources. Healthcare is covered at 100% for employees on the gold plan, and 50% for dependents.
  • Professional Development: Annual $1K learning stipend to use toward classes, certifications, conferences, or other meaningful career development.
  • Equity Ownership: As a fast-growing startup, we offer equity to ensure that you share in our success as we grow together.
  • Paid Time Off: Unlimited PTO policy with an encouraged three-week annual minimum.
  • Team Events: We regularly host virtual team social activities and happy hours, and travel to meet in-person 1-2 times a year.
  • Competitive Salary: We provide a salary that reflects your skills and experience, along with opportunities for performance-based bonuses. Salary range: $140,000 - $172,000 annually depending on skillset and experience.

Siteline provides a construction billing software designed specifically for subcontractors to generate, submit, and manage pay applications. It acts as a central hub for accounts receivable, enabling collaboration among teams and keeping all pay-app-related documents in one place. The platform Tailors pay apps to each general contractor’s specifications and tracks compliance documents to reduce errors and delays. This helps streamline the billing workflow, cut down on missing or incorrect information, and improve cash flow by reducing payment delays. Siteline has processed over $1 billion in billing across more than 10,000 projects, indicating real-world use in the construction market. The company likely operates on a subscription model where subcontractors pay a recurring fee for access. Overall, Siteline aims to simplify and speed up the subcontractor billing process so contractors get paid faster and more reliably.

Company Size

11-50

Company Stage

Series A

Total Funding

$18.4M

Headquarters

San Francisco, California

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Customers get paid 3 weeks faster with 6x billing efficiency.
  • Siteline processed over $10B across 200k+ projects since 2019.
  • Menlo Ventures led $15M Series A in February 2022.

What critics are saying

  • Procore's billing module erodes Siteline's share in 6-12 months.
  • Autodesk captures MEP users via BIM integration in 12-18 months.
  • NY mandates digital pay apps by Q3 2026, obsoleting templates.

What makes Siteline unique

  • Siteline digitizes 23,000+ pay app forms from 17,000+ GCs.
  • Siteline automates lien waivers and state-specific compliance tracking.
  • Siteline integrates with QuickBooks, Procore, and Foundation Software.

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Your Connections

People at Siteline who can refer or advise you

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Flexible Work Hours

Remote Work Options

Unlimited Paid Time Off

Professional Development Budget

Equity Options

Team Events

Growth & Insights and Company News

Headcount

6 month growth

-2%

1 year growth

-4%

2 year growth

2%
Silicon Valley Daily
May 19th, 2023
Ethernovia Scores $64 Million

SAN FRANCISCO — Siteline, developer of an advanced billing solution for commercial trade contractors, has reeled in a $15 million Series A funding round led by Menlo Ventures with participation from existing investors.

Silicon Valley Daily
Mar 1st, 2023
VC Firm SignalFire Closes $900 Million in New Capital

SAN FRANCISCO — Siteline, developer of an advanced billing solution for commercial trade contractors, has reeled in a $15 million Series A funding round led by Menlo Ventures with participation from existing investors.

PYMNTS
Feb 13th, 2023
30% Of Construction Firms Are Investing In Technology

Construction firms are looking to technology to help them improve operations and build resilience. . Thirty percent of such firms said they are preparing for a possible recession by investing in technology to save time and costs, according to the January/February edition of the “B2B and Digital Payments Tracker®,” a PYMNTS and American Express collaboration. . They’re planning to add technology to accelerate payments, reduce financing costs and streamline back-office processes — solutions that address common problems in the construction industry, according to the report.

Informa Markets
Sep 7th, 2022
Label Traxx partners with Siteline

For the last six years, Label Traxx has collaborated with Siteline to develop and deploy a web-to-print technology that enables label customers and distributors to reorder, approve the artwork, pay invoices, and manage their label product catalogs online.

Silicon Valley Daily
Mar 7th, 2022
Menlo Ventures invests into Siteline in $15M

SAN FRANCISCO — Siteline, developer of an advanced billing solution for commercial trade contractors, has reeled in a $15 million Series A funding round led by Menlo Ventures with participation from existing investors.

INACTIVE