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AI Products - Pre-sales & Customer Success Specialist

Reddico

Reddico

Software Engineering, Sales & Business Development, Data Science, Customer Service
Toronto, ON, Canada
USD 85k-100k / year
Posted on Feb 26, 2026
GAIN is a creative-led, insight-driven company that blends data, tech and creativity. We believe the best ideas emerge where intelligence and creativity unite, where insight sparks imagination, and where innovation turns possibility into progress.

We are explorers of new frontiers, shaping bold strategies that move people, brands, and businesses forward. Individually and together, our specialist teams provide the vision, data, and confidence brands and organizations need to make braver, more impactful decisions.

Today as GAIN, we work as a united force, using data to fuel creativity, and technology to unlock new possibilities. As imagineers we don't just embrace innovation - we engineer it, transforming information into action, and ideas into breakthroughs.

This is where rebel thinking, smart technology, and data-driven creativity shape the future.

Through our five specialist teams: Creative Studio, Conversion, Customer Science, Experience and Performance. Individually, and together, we work to fuel your growth and deliver measurable impact.

The Role

We are seeking an AI Products - Pre-sales & Customer Success Specialist to become the primary client-facing specialist for GAIN's AI product suite, with an initial focus on two AI products: one centered on Performance Creative and the other on Conversion Rate Optimization (CRO). You will lead discovery and solutioning with prospects whose needs go beyond self-service, delivering compelling demos, shaping proposals, and positioning the right combination of GAIN products and services. In addition, you will oversee onboarding and early success for clients purchasing higher-tier subscriptions, ensuring they realize value quickly and are set up for long-term adoption.

This role sits at the intersection of product, sales, and customer success, working closely with the Chief Digital Officer, Product, Engineering, Performance, Conversion, Services and Operations teams.

Responsibilities

Pre-sales & Solution Consulting

  • Lead discovery conversations with prospects to understand business context, performance challenges, and AI maturity, especially across performance creative and Conversion Rate Optimization (CRO).
  • Deliver structured, tailored demos of GAIN's AI products, showcasing how the platforms support end-to-end journeys from acquisition and creative testing through conversion optimization
  • Translate prospect requirements into concrete solution architectures that combine GAIN's AI tools with relevant GAIN services (e.g., Performance, Experience, Conversion).
  • Partner with sales and marketing to shape proposals, statements of work, and subscription recommendations for mid-market and enterprise opportunities.
  • Capture and organize prospect feedback and objections, feeding it back into product roadmaps, positioning, and collateral.

Demos, Enablement & GTM Support

  • Own the end-to-end demo program for higher-touch prospects: scheduling, preparation, configuration of demo environments, and follow-up materials.
  • Collaborate with Product owners, Marketing and Digital teams to keep demo scripts, narratives, and collateral aligned with the latest product capabilities and GTM priorities.
  • Support webinars, events, and field marketing with live demos and Q&A, representing GAIN's AI products to growth, marketing, and services teams.
  • Help define and refine qualification criteria and playbooks for when prospects should receive high-touch demos versus self-service experiences.
  • Comfortable representing GAIN's AI products externally, including for demos, webinars, product walkthroughs, and presenting thought leadership content
  • Sharing product perspectives, learnings, and use cases in collaboration with Marketing and Product teams on relevant social media platforms such as LinkedIn

Customer Onboarding & Success

  • Lead onboarding for clients purchasing higher-tier subscriptions, from kick-off through initial activation and first value.
  • Map client use cases to platform features, designing onboarding plans, success criteria, and measurement frameworks tied to performance outcomes.
  • Work with clients to set up integrations, workflows, and initial experiments (e.g., creative testing plans, CRO hypotheses) in collaboration with GAIN's specialist teams.
  • Monitor early usage and performance, proactively intervening with training, office hours, or playbook recommendations to drive adoption and renewal readiness.

Internal Collaboration & Product Feedback

  • Act as the voice of the customer in product stand-ups and planning sessions, feeding in insight from demos, sales cycles, and onboarding.
  • Coordinate with Product, Engineering, and Operations to ensure smooth handoffs from sale to onboarding to steady-state success.
  • Partner with the Client Advisory Board and key accounts to surface structured feedback on roadmap, usability, and outcomes.
  • Contribute to internal enablement, helping sales and account teams understand product capabilities, ideal customer profiles, and key use cases.

Measurement & Continuous Improvement

  • Track funnel and success metrics related to pre-sales motions: demo-to-opportunity, opportunity-to-close, and time-to-value post-onboarding.
  • Use product analytics, CRM, and feedback logs to identify patterns in successful implementations and refine playbooks accordingly.
  • Work with Operations to ensure relevant events, lifecycle stages, and campaign associations are captured in tools such as HubSpot and analytics platforms.

Requirements

The ideal candidate has the following qualifications, but we encourage you to apply even if you feel you do not meet 100% of the requirements below.

  • 4-6 years in B2B SaaS in a client-facing role such as pre-sales, solutions consulting, customer success, or product specialist, ideally within AI, data, marketing technology, or CRO/performance advertising domains.
  • Demonstrated experience delivering tailored software demos and discovery sessions for marketing, growth, or digital teams.
  • Strong familiarity with performance marketing and/or CRO concepts (e.g., creative testing, funnel optimization, experimentation) and the ability to link them to platform capabilities.
  • Experience collaborating with sales, product, and delivery teams to shape solutions and execute go-to-market plans.
  • Comfortable working with CRMs and GTM tools (e.g., HubSpot, Salesforce, outreach platforms) to manage pipelines, activities, and reporting.
  • Excellent communication and storytelling skills, with the ability to translate technical features into clear business value for different audiences.
  • Proven ability to operate in fast-paced, ambiguous environments, managing multiple opportunities and onboarding projects in parallel.

Skills And Attributes

  • Customer-centric mindset with a strong focus on value realization and long-term relationships.
  • Confident facilitator for live demos, workshops, and onboarding sessions, both remote and in person.
  • Analytical and structured, able to interpret performance data and client feedback to inform next steps and recommendations.
  • Highly collaborative, comfortable working across Product, Marketing, Sales, Operations, and Services teams
  • Proactive, resourceful, and comfortable taking ownership from initial prospect contact through to early customer success.

Benefits

  • Hybrid work environment + a home office allowance
  • Flex-Fridays! Friday is your uninterrupted day to wrap up the work week or sign off early
  • 3 weeks of paid time off to start, plus a winter holiday office closure.
  • Work from anywhere in the world up to 20 business days or 4 weeks per year! We want you to build a life and a career at the same time
  • Wellness time, health + dental coverage, health spending account, and wellness spending account so that you can prioritize YOU
  • Reward + recognition programs to recognize your team (and be recognized) for all that we do
  • Work at a certified Great Place to Work®

GAIN is an equal opportunities employer and positively encourages applications from suitably qualified and eligible candidates regardless of sex, race, disability, age, sexual orientation, gender reassignment, religion or belief, marital status, or pregnancy and maternity. We believe that diversity and inclusivity make our teams better, so it is our priority to create an equitable and inclusive workplace where our goals, initiatives, and commitments to action are shaped and strengthened by our team's voices. Putting People First, one of our core values, means we never lose sight of humanity, care, and impact.

Pay range - The typical hiring range for this role is $85,000 - $100,000 annually. This range reflects our commitment to our compensation philosophy, internal equity, and comes with a competitive and comprehensive total rewards package. Base pay will be determined based on role-related skills, knowledge, and experience.

Disclaimer: we never request any form of payment or fees from candidates at any stage of the recruitment process. If you are contacted by anyone claiming to represent our company and asking for money or personal financial details, please report it immediately to people@thisisgain.com. All genuine communication will come from official company channels.