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PayShepherd Job Board

Customer Success Manager

remote
Calgary, AB, Canada .
full-time . September 16, 2026

Description

PayShepherd envisions a future where heavy industrial sites operate with maximum efficiency and minimal administrative burden. Our strategy focuses on building a comprehensive and user-friendly contractor management platform, fostering better relationships between contractors and clients and ensuring project success.
We have an aggressive growth plan and are looking to add to our team. You’d be a great fit to execute on this vision if you: 

  • Thrive in a fast-paced, ever evolving environment
  • Are passionate about bringing innovation to transitional industries 
  • Have experience in Heavy Industry or Technology 
  • Are proactive at creating creative solutions to complex problems
  • Are client focused, our success is built on strong relationships between us, our clients and their contractors. If you excel at collaboration and are committed to delivering exceptional service you’ll fit right in 
  • Treat AI as a core part of how you work.
We are looking for a Customer Success Manager to join our Customer Success team. You are our product expert and delivery engine, and in partnership with the Relationship Manager, you bring proof of the value. Your focus is time to first value (TTFV), user adoption, value attribution, and customer sentiment.
What we value: 

  • Customer Centric: strives to create delightful experiences, make customer lives easier, and be a trusted partner to clients and their contractors.
  • Builds Trust: demonstrates open and clear communication in all interactions, holds themselves accountable, and is respectful to colleagues, customers, and partners.
  • Bias for Action: moves work forward by taking the next step rather than stopping at opinions, keeps timelines tight, and maintains deliberate momentum to drive results.
  • Growth Mindset: values resilience and believes effort leads to improvement; treats mistakes as stepping stones, welcomes feedback, and prioritizes outcomes over ego by evaluating ideas on their merit.
  • Deep Curiosity: asks a lot of questions, digs into hard problems, challenges their own thinking, and keeps experimenting rather than settling for what is already known.

Primary Responsibilities: 

  • Identify and execute on client value opportunities. Discover pain, find value. Build the plan. Deliver it. 
  • Understand what each client values, and keep understanding it. At point of sale, as the champion evolves, and as the org changes. Stay attuned at the product and user level: what are users experiencing, and what has changed?
  • Own value attribution, and be obsessive about it. Document to the value vault continuously: cost savings, time saved, risk reduced, process improved. Feed it to the RM. No value goes unrecognized.
  • Advocate for the customer inside PayShepherd. You are the customer's voice to Product, Engineering, and leadership. Create and follow up on idea tickets using existing processes, not side spreadsheets.
  • Drive adoption by understanding what users care about. Connect the platform to what they specifically need. Show them the value in their terms, not ours.
  • Run a detractor management plan on every account. Know every detractor by name. Have a plan for each one. Convert detractors to neutrals and neutrals to advocates. No detractor goes unmanaged.
  • Build advocacy with ICs and managers, and drive insights upward. Make users into champions. Surface what you learn from the operational floor to the people who can influence decisions. The RM owns the director-level relationship; you own the intelligence that makes it valuable.
  • Capture client referrals and references. When a customer sees value, lock it in. Turn advocates into references, case studies, and referrals that fuel growth.
  • Own client NPS. You own customer sentiment. NPS is your signal and scorecard. Track with quality: no duplicate outreach, meaningful follow-up.
  • Deliver implementations that create first value fast. Config, training, go-live, and contractor onboarding. You bring the product expertise. Work with the RM to get to first value quickly.
  • Collaborate across teams. Mobilize Support (under Tracy) for contractor issues. Work with Product, Engineering, and the RM to drive outcomes. Your time stays on strategic delivery, not tickets.
  • Build and maintain AI-assisted workflows across the customer success motion (onboarding, training, health monitoring, support and account planning) so you can deliver faster and serve more customers.
  • Use AI to analyze customer usage and data, surface adoption gaps and churn risk, and turn it into clear actions and customer-ready summaries.
  • Automate the repetitive parts of your work (meeting notes, status reports, QBR prep, first-pass support responses) so your time goes to relationships and outcomes.
What you need to succeed / what will set you apart

  • Understanding of heavy industry (oil and gas, mining, manufacturing, pulp and paper etc.) 
  • Using strong business acumen and project management best practices to maximize revenue by minimizing the time needed to onboard new business opportunities.
  • Self-driven commitment to keep learning; our product evolves fast and so do our customers
  • Creative problem solving skills resulting in practical and innovative solutions
  • Excellent communication and presentation skills
  • Strong organizational skills, internal and external teams will depend on you
  • 3+ years of CSM experience or in a SaaS organization would be considered an asset
  • Strong analytical skillset with the ability to interpret dashboards and data trends
  • Eagerness to climb the AI proficiency ladder quickly. The expectation for this role is that you reach Builder level, automating real parts of your own job, and keep going
  • You enjoy a cross-functional role where you get to collaborate outside of your immediate team (product, marketing, sales, etc.)
  • Ability to build and nurture strong relationships
  • You enjoy customer-facing interactions and have a commitment to providing outstanding customer service
  • Willing and able to travel occasionally within Canada and to the US
  • Strong Microsoft Office (Excel, PowerPoint, MS Project) and Google Suite skills (Google Drive, Gmail, Google Sheets, Google Pages), plus comfort adopting new AI tools quickly
  • Bilingual in English with French or Spanish would be considered an asset, although not required. 
What you will enjoy

  • Remote work
  • Qualify for variable compensation based on annual goals
  • Flexibility, professional development, internal mobility, high growth environment, intrinsically rewarding work, self-determination, day to day variety, stock options
  • Best-in-class AI tools with no token limits, and a culture that funds and celebrates building with AI
Compensation

  • Full-time, Permanent, base salary of $60,000 -$90,000 per year based on experience, qualify for variable compensation based on quarterly goals plus attractive stock options plan
  • Extended Health Benefits Package
How to Apply

PayShepherd is committed to achieving workforce diversity and creating an inclusive working environment. Diversity makes sense for us, for our customers and our future. We value different perspectives, skills, and experiences, and welcome applications from all sectors of the community.

We welcome candidates with disabilities and will make accommodations throughout all stages of the recruitment and selection process. If you require a disability-related accommodation, please get in touch with us directly.
All candidates must satisfy a background check.
We thank all applicants for their interest, and only those selected for an interview will be contacted.

Compensation

$60,000.00 - $80,000.00 per year

Know someone who would be a perfect fit? Let them know!