Jobs at Trolley (Now Hiring) — 23 open — Page 2

Solutions Engineer

Location: Based in our Halifax, Montreal, or Toronto office, supporting global customers
Proposed OTE: $135k CAD ($100k base, $35k variable)

About Trolley

Trolley is a leading payouts platform that helps businesses automate payouts, recipient onboarding, tax workflows, and verification for contractors, creators, sellers, and partners around the world. We combine flexible payout infrastructure with embedded developer tools so customers can launch faster, reduce manual work, and deliver a better recipient experience.

We’re expanding our team and looking for a highly technical Solutions Engineer to support our sales process and help customers design scalable solutions using Trolley’s platform.

Role Overview

As a Solutions Engineer at Trolley, you’ll help prospects determine whether our platform fits their needs and what it will take to implement it and help existing customers expand their use of Trolley to accomplish more. You’ll work with technical and business stakeholders to understand their systems, workflows, compliance requirements, and recipient experience goals, then recommend a practical approach using Trolley’s APIs, SDKs, widgets, webhooks, and integrations.

You should be comfortable leading technical discovery, discussing architecture and implementation details, and running demos for both technical and non-technical audiences. The role covers more than payouts, so you’ll also need to speak to onboarding, tax, verification, trust, and related workflows when needed.

Your time will be focused 80% on new business solutioning with Sales and Partnerships and 20% on supporting existing customers expand their integration with our Customer Success team.

Key Responsibilities

Technical Discovery & Solution Design

• Lead technical discovery with prospects to understand their architecture, workflows, integration requirements, compliance considerations, and operational needs.
• Design scalable solution approaches using Trolley’s APIs, SDKs, widgets, embedded onboarding flows, app integrations, and automation capabilities.
• Help customers evaluate implementation options based on their internal resources, timelines, and desired recipient experience.
• Translate business requirements into technical solution designs, integration recommendations, and phased rollout plans.
• Advise on data flows, authentication, configuration, implementation sequencing, and long-term maintainability.

Product Demos & Technical Validation

• Deliver customized product demos that clearly connect Trolley’s capabilities to a customer’s technical environment and business goals.
• Build and present proofs of concept, sample workflows, and technical validations to help prospects assess feasibility and accelerate decision-making.
• Answer detailed technical questions related to APIs, webhooks, widgets, onboarding flows, payout operations, and implementation best practices.
• Support security reviews, technical questionnaires, integration discussions, and RFP What do responses as needed.

Implementation Support

• Partner with Customer Success during complex implementations to ensure continuity from pre-sales design through to onboarding and launch.
• Help customers validate requirements, navigate integration blockers, and align technical workstreams during rollout.
• Leverage best practices to guide customer implementations and ensure long-term sustainability of their solution.
• Support sandbox testing, implementation planning, and solution reviews for strategic or technically complex customers.
• Reduce implementation risk by ensuring the proposed solution is realistic, well-scoped, and aligned with customer systems and resources.

Cross-Functional Collaboration

• Work closely with Product and Engineering to communicate customer feedback, recurring technical objections, product gaps, and emerging use cases.
• Build and contribute to internal technical assets such as demo environments, integration playbooks, sample workflows, and reusable solution materials.
• Create and expand tools to empower the broader sales team to be more effective and efficient, by gathering and synthesizing technical information and utilizing tools to enable AEs and CSMs to provide fast and accurate answers and improve positioning.
• Design and create tools and content to enable self-guided product discovery by prospects.

Requirements

Technical Skills

• Strong experience working with APIs, including writing documentation, testing endpoints, understanding request and response structures, and supporting customer integrations.
• Solid understanding of REST APIs, webhooks, authentication methods, JSON payloads, and common SaaS integration patterns.
• Experience with technical tooling such as Postman, Swagger or OpenAPI documentation, and sandbox environments.
• Familiarity with embedded product experiences, workflow automation, and systems integration.
• Ability to understand and explain technical tradeoffs clearly to both technical and non-technical audiences.
• Experience and proficiency building solutions with AI-tooling

Experience

• 3+ years in a Solutions Engineer, Sales Engineer, Technical Consultant, Implementation Consultant, or similar customer-facing technical role, ideally in SaaS or fintech.
• Proven experience supporting mid-market and enterprise sales cycles with meaningful technical discovery and solution design.
• Experience helping customers plan and implement software integrations in production environments.
• Experience with payment infrastructure, global payouts, tax workflows, verification, or compliance-related products is a strong plus.

Core Competencies

• Technical Depth: Able to lead credible conversations around integrations, architecture, data flows, and implementation planning.
• Customer Focus: Able to understand customer goals and map them to practical solutions that deliver measurable value.
• Communication: Strong presenter who can explain complex technical concepts clearly and persuasively.
• Problem Solving: Comfortable navigating ambiguity, diagnosing challenges, and proposing realistic implementation paths.
• Collaboration: Works effectively across Sales, Customer Success, Product, and Engineering.

Geographic Scope

• • Comfortable working with US-based clients, with occasional support for clients in Europe and Australia.

What We Offer

• Competitive base salary and variable pay
• Collaborative Culture: Work closely with cross-functional teams in a supportive and innovative environment.
• Growth Opportunities: Be part of a rapidly expanding company with opportunities for career development.
• Extended Healthcare benefits including dental, vision, LTD, etc. from day 1.
• 4 weeks paid vacation per year + public holidays (+ 1 extra vacation day per year of service).
• 30 days remote work from anywhere.
• Gym membership allowance.
• 1/2 day Fridays off during summer.
• Company-provided use of Apple MacBook Pro and Mac gear.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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