We’re hiring · 6 open roles

Help contractors win back their time

DripJobs is the all-in-one CRM trusted by 2,500+ painting and home service contractors across the US and Canada. We’re a fully remote team, we’re growing, and we’re looking for people who want to do the best work of their careers helping the trades.

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Built by a contractor

Our founder ran a $1.5M painting company before building DripJobs. We know our customers because we’ve been our customers.

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Bootstrapped and fully remote

No outside investors, and a fully remote team around the world. We grow by making customers successful, and every person on the team has a real impact on that.

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People before profit

We treat customers like people, not tickets or deals, and we treat each other the same way.

Open roles

Click a role to see the details, then apply below.

SalesSales Development Representative (SDR)Full-time · Remote

Full-time, remote Sales Development Representative. Your one job: book 15+ high-quality demos a month on our Senior Account Executive’s calendar. This is a quality-over-quantity role. A demo only counts when the right decision maker shows up. You’ll make around 50 consistent outbound calls a day, working lists we provide and leads you find yourself.

What you’ll do

  • Make 50+ outbound calls a day in Close CRM to contractors from event lists, Facebook groups, map searches, and self-sourced leads
  • Prospect on Facebook, Instagram, LinkedIn, Alignable, and more
  • Qualify every demo: the decision maker (or a strong influencer) is on the call, and the business fits our industries: painting, concrete/flooring, foundation repair, asphalt/paving, gutters, deck/fence, exterior services, cabinet refinishing, junk removal, and pool installation
  • Log each demo in your Close Smart View with company, website, contact name, phone, email, and notes for the AE
  • Confirm booked demos so they show up, which can mean confirming with the prospect several times before the call with the AE

What we’re looking for

  • Fluent, clear spoken English. You’ll be calling US and Canadian business owners all day
  • 3+ years of quality-focused outbound: booking and confirming demos
  • Comfortable with rejection and steady daily volume
  • Organized in a CRM; experience with Close is a plus
  • Outbound experience at scale is a plus
  • Reliable high-speed internet, a quality headset, and a quiet workspace
SalesAccount Executive (AE)

You run live demos for contractors, show them how DripJobs fits the way they work, and help them choose the right plan. You close by understanding the business, not by pushing.

What you’ll do

  • Run consultative product demos for painting and home service contractors
  • Build a plan around each prospect’s needs, including add-ons and extra users
  • Manage your pipeline and follow-ups through to a closed deal
  • Hand new customers off to onboarding with clear notes so they start strong

What we’re looking for

  • A track record of closing in a sales role, ideally SaaS or the trades
  • You can explain software in plain language to busy business owners
  • You’re honest about what the product does and doesn’t do
  • You’re disciplined about pipeline hygiene and follow-up
SupportCustomer Support Representative

You help contractors get unstuck. When someone has a question about proposals, drips, invoicing, or anything else in DripJobs, you’re the person who gets them a clear answer fast.

What you’ll do

  • Answer customer questions through live chat and email
  • Troubleshoot issues, reproduce bugs, and escalate them clearly to the product team
  • Walk customers through features so they get more out of DripJobs
  • Help keep our help center articles accurate and up to date

What we’re looking for

  • Patient, friendly, and clear in writing
  • You enjoy figuring out how software works
  • You take ownership of a problem until it’s solved
  • Previous customer support or SaaS experience is a plus
SupportCustomer Support ManagerFull-time · Remote · People manager · Reports to the Customer Success Manager

The Customer Support Manager sits at the heart of the DripJobs customer experience. You’ll own the team’s Intercom platform and the customer touchpoints for advanced features and training, social media engagement, and the nurturing communication that runs through the customer’s journey. You’ll develop and scale team performance with strong organizational and technical skills, making sure every interaction across every tier meets the DripJobs standard for speed and quality, with a customer-centric approach rooted in gratitude and helpfulness.

This role requires hands-on, deep knowledge of the DripJobs software: the expertise to guide technical escalations and coach the team through complex issues. That technical strength is balanced by a customer-first mindset that keeps the customer experience at the center of every decision. As a member of the leadership team, cross-functional collaboration, innovation, and clear communication are essential.

What you’ll own

Team quality & performance
  • Own the quality standard across Support Specialist and Team Lead interactions: review Intercom conversations, session recordings, knowledge base articles, and call review reports against our quality rubric, and partner with the Team Lead to deliver coaching
  • Treat CSAT as the team’s primary quality signal: review feedback daily, analyze it monthly, and keep SOPs current before any process change takes effect, recommending updates to the Customer Success Manager
The customer success lifecycle
  • Make sure every support interaction strengthens the customer’s long-term success with DripJobs, from their first questions after go-live through years of growth, treating each conversation as part of a lasting relationship rather than a single ticket
  • Equip the team to help customers adopt features that grow their business, with feature training that turns support conversations into opportunities to deepen product value and build loyalty
  • Partner with the Onboarding team on seamless handoffs at each lifecycle stage, so no customer falls through the gaps
  • Keep designated customer communication timely, including touchpoints, nurturing, and product and event releases
  • Use our at-risk customer dashboard, CSAT, Intercom conversation trends, and escalation patterns to spot customers showing signs of frustration or disengagement, and flag them for proactive outreach
Capacity, coverage & escalations
  • Monitor capacity and individual workload against support volume, keep every channel covered during operating hours, and adjust schedules proactively with evidence-based staffing recommendations
  • Own the escalation framework across tiers: review escalation rates weekly to separate training gaps from judgment gaps, and document complex resolutions that fall below standard for team learning
Release readiness & product partnership
  • Partner with Product and Development on every release: secure early access for the Team Lead and key Specialists, assess expected support volume before launch, and sync team readiness with customer communication
  • Route team-reported bugs, product questions, and enhancement requests through the product team’s triage process with complete context, and turn CSAT trends, escalation patterns, and recurring friction into structured, data-backed product feedback
  • Keep the team briefed on every active known issue so no one is caught off guard in a live interaction
  • Schedule customer-facing advanced sessions (Job Costing, Production Rates, Zapier, and more) delivered by the team’s designated Specialist, and partner with Development, Operations, and Success on proactive outreach for widespread issues
Hiring, onboarding & team development
  • Own the full hiring process for Customer Support roles, from defining the role with the Customer Success Manager through structured interviews and documented, evidence-based hiring decisions
  • Partner with the Team Lead on a structured onboarding program with shadowing, daily coaching, and competency sign-off before live interactions
  • Run 30/60/90-day and annual evaluations that each produce a documented outcome and follow-up date
Reporting & leadership insights
  • Deliver a weekly support summary and a monthly metrics review to the Customer Success Manager and leadership team, with 2–3 written insights that translate support data into what it means for retention and product
  • Celebrate wins publicly, and share successes, challenges, and recommendations in weekly 1:1s with the Customer Success Manager and biweekly 1:1s with the Team Lead and Support Specialists

What we’re looking for

  • 3+ years in Customer Support or Customer Success, including 1+ year leading or coaching a support team
  • A track record of managing to support KPIs such as CSAT, response time, and escalation rate in a SaaS environment
  • Hands-on experience with Intercom or a similar support platform; experience serving small business or home service customers is a plus
  • Fluent written and spoken English; bilingual is preferred but not required
  • A coaching-oriented leader who frames performance conversations as development, not discipline
  • The ability to turn support metrics into clear insights and decisions for leadership
  • Level-headed and organized under pressure, with strong cross-functional communication
  • You lead with a customer-first approach, kindness, and gratitude

What success looks like

  • Team CSAT above 92%, with Tier 1 first response under 3 minutes and Tier 2 under 2 minutes
  • Complex resolution and go-live success rates above 95%; proper Tier 1 escalation above 90% and escalation to Tier 3 below 15%
  • A current knowledge base, with 60 articles updated and 40 new articles created each month
  • No release reaches customers before the support team is ready for it
  • Team-reported issues reach the product team with full context, and a monthly CSAT trend report shapes product and process decisions
  • Weekly social media posts or videos, and a team culture where wins are recognized and every hire raises the bar
EngineeringDevelopment QA

You make sure what we ship works for the contractors who rely on it every day. You test new features before they go out and catch problems before customers do.

What you’ll do

  • Test new features and releases across our web app and mobile app
  • Write and maintain test cases and regression checklists
  • Reproduce reported bugs and document them clearly for developers
  • Work with engineering and support to verify fixes before release

What we’re looking for

  • Experience in software QA or testing
  • Very detail-oriented, with clear, reproducible bug reports
  • Comfortable with bug trackers and testing tools
  • Experience with test automation is a plus
PartnershipsPartnership Assistant

You help us grow through the companies and communities contractors already trust. You keep our partner relationships organized and our partner programs running smoothly.

What you’ll do

  • Coordinate with partners on co-marketing, webinars, and referral programs
  • Help organize trade shows and industry events
  • Track partner referrals and keep partner records up to date
  • Prepare partner materials and follow up on open items

What we’re looking for

  • Highly organized, with strong follow-through
  • Friendly and professional in writing and on the phone
  • Comfortable juggling several projects and deadlines
  • Interest in the trades or the home service industry

Apply to DripJobs

Tell us a bit about yourself and attach your resume. We review every application.

DripJobs is an equal opportunity employer. We welcome applicants of every background and do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic.