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About Highspring

Highspring is a next-generation consulting and professional services firm. We deliver modern, agile, and forward-thinking solutions to our clients across North America. We work with some of the most innovative companies in banking, insurance, and technology to help them build the future. At Highspring, we believe in empowering our people, fostering leadership, and delivering real business impact.

The Opportunity

Highspring is seeking an experienced Scrum Master to support a large-scale insurance product transformation initiative. This engagement focuses on modernizing and enhancing an existing coverage product by aligning it with new standards, updating coverage content, improving the user experience, implementing custom business rules, and integrating optional coverage offerings.

With most APIs and backend services already established, the team will focus on product delivery, execution, and continuous enhancement within an Agile environment.

You will collaborate closely with a Project Lead and a hybrid team of consultants and permanent employees to ensure successful delivery across one or more Agile squads.

What You’ll Do

• Act as Scrum Master for one or more Agile delivery teams.
• Facilitate Agile ceremonies, including sprint planning, daily stand-ups, sprint reviews, and retrospectives.
• Promote Agile best practices and help ensure team alignment, transparency, and continuous improvement.
• Remove delivery obstacles and support issue resolution across teams and stakeholders.
• Coordinate with business and technology stakeholders to maintain project momentum and delivery quality.
• Support delivery activities through occasional project coordination, business analysis, or functional analysis contributions when required.
• Foster strong collaboration between business and IT teams.
• Track and communicate progress, risks, and dependencies in a fast-paced delivery environment.
• Help ensure the team remains focused on meeting project objectives and timelines.

What You Bring to the Table

• Proven experience serving as a Scrum Master within Agile delivery environments.
• Demonstrated ability to facilitate collaboration across cross-functional teams.
• Strong communication, stakeholder management, and facilitation skills.
• Solid understanding of business analysis and functional analysis principles.
• Ability to adapt quickly and contribute beyond traditional Scrum Master responsibilities.
• Strong organizational, problem-solving, and conflict-resolution skills.
• Experience working in complex IT project environments.
• Comfortable operating in fast-moving projects with ambitious delivery timelines.

Core Skills Required

• Scrum Master experience in Agile software delivery teams.
• Strong knowledge of Agile methodologies and frameworks.
• Business analysis and functional analysis expertise.
• Stakeholder engagement and communication.
• Team facilitation and coaching.
• Risk, dependency, and issue management.
• Cross-functional collaboration.
• Project coordination and delivery support.

Our Stack

While this role is not hands-on technical development, the project includes:

• Modern web and digital customer experiences.
• Existing API and microservices-based architecture.
• Agile product delivery practices.
• Cross-functional business and technology teams.

Why Join Highspring?

• Work alongside experienced consultants and delivery professionals on a high-impact transformation initiative.
• Contribute to a strategic program within the insurance industry.
• Gain exposure to large-scale Agile delivery and modern product transformation.
• Join a collaborative and flexible consulting environment focused on delivering business value.
• Opportunity for contract extension beyond the initial engagement.

Location: Montreal, QC (Hybrid – 2 days onsite per week)

Contract Length: Initial 6-month contract

À propos de Highspring

Highspring est une firme de consultation et de services professionnels de nouvelle génération. Nous offrons des solutions modernes, agiles et innovantes à nos clients partout en Amérique du Nord. Nous collaborons avec certaines des entreprises les plus novatrices des secteurs financiers, de l’assurance et de la technologie afin de les aider à bâtir l’avenir. Chez Highspring, nous valorisons le leadership, le développement de nos talents et la création d’un impact concret pour nos clients.

L’opportunité

Highspring est à la recherche d’un(e) Scrum Master expérimenté(e) pour contribuer à une importante initiative de transformation d’un produit d’assurance.

Le projet vise à moderniser et faire évoluer un produit de couverture existant en l’alignant sur de nouveaux standards, en mettant à jour son contenu, en améliorant l’expérience utilisateur, en implantant des règles d’affaires personnalisées et en intégrant des produits de couverture optionnels.

Comme la majorité des API et des microservices sont déjà en place, l’équipe pourra se concentrer sur la livraison, l’amélioration continue du produit et l’atteinte des objectifs d’affaires.

Vous travaillerez en étroite collaboration avec le responsable du projet ainsi qu’une équipe hybride composée de consultants et d’employés permanents.

Ce que vous ferez

• Agir à titre de Scrum Master auprès d’une ou plusieurs équipes Agile.
• Animer les cérémonies Agile, incluant la planification des sprints, les rencontres quotidiennes, les revues de sprint et les rétrospectives.
• Promouvoir les meilleures pratiques Agile et favoriser l’amélioration continue.
• Assurer l’alignement, la transparence et l’efficacité des équipes.
• Identifier et éliminer les obstacles pouvant affecter la livraison.
• Collaborer avec les parties prenantes d’affaires et technologiques afin de soutenir l’avancement du projet.
• Participer occasionnellement à des activités de coordination de projet, d’analyse d’affaires ou d’analyse fonctionnelle selon les besoins.
• Favoriser la collaboration entre les équipes d’affaires et les équipes TI.
• Assurer le suivi des risques, dépendances et enjeux de livraison.
• Contribuer au maintien de la qualité et du rythme de livraison dans un environnement dynamique.

Ce que vous apportez à l’équipe

• Expérience démontrée à titre de Scrum Master dans des environnements de livraison Agile.
• Excellentes aptitudes en communication, animation et gestion des parties prenantes.
• Bonne compréhension des concepts d’analyse d’affaires et d’analyse fonctionnelle.
• Expérience de travail auprès d’équipes multidisciplinaires dans des projets TI.
• Capacité à s’adapter et à contribuer au-delà des responsabilités traditionnelles d’un Scrum Master.
• Solides habiletés en résolution de problèmes et en gestion des priorités.
• Approche collaborative et orientée vers les résultats.
• Aisance à évoluer dans des projets à échéanciers serrés et à forte visibilité.

Compétences clés requises

• Expérience en gestion Agile et en animation Scrum.
• Excellente maîtrise des principes et cadres Agile.
• Analyse d’affaires et analyse fonctionnelle.
• Gestion des parties prenantes.
• Facilitation et coaching d’équipes.
• Gestion des risques, dépendances et enjeux.
• Collaboration interfonctionnelle.
• Coordination de projet et soutien à la livraison.

Notre environnement

Bien que ce rôle ne soit pas un poste de développement technique, le projet comprend :

• Des expériences numériques modernes destinées aux utilisateurs.
• Une architecture reposant sur des API et des microservices existants.
• Des pratiques de livraison Agile.
• Une collaboration étroite entre les équipes d’affaires et technologiques.

Pourquoi joindre Highspring?

• Faites partie d’une équipe de consultants et de professionnels de la livraison reconnue pour son expertise.
• Contribuez à une transformation stratégique dans le secteur de l’assurance.
• Développez votre expérience dans des programmes Agile d’envergure.
• Profitez d’un environnement de travail collaboratif, flexible et axé sur les résultats.
• Bénéficiez d’un fort potentiel de prolongation après la durée initiale du mandat.

Lieu : Montréal, QC (mode hybride – 2 jours par semaine au bureau)

Durée du mandat : 6 mois initialement

By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions.

EEO Notice

Vaco by Highspring is an Equal Opportunity Employer and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by federal, state or local law.

Vaco by Highspring and its parents, affiliates, and subsidiaries are committed to the full inclusion of all qualified individuals. As part of this commitment, Vaco by Highspring and its parents, affiliates, and subsidiaries will ensure that persons with disabilities are provided reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact HR@vaco.com.

Vaco by Highspring also wants all applicants to know their rights that workplace discrimination is illegal.

Representation Notice

By submitting to this position, you agree that you will be giving Vaco by Highspring the exclusive right to present your as a candidate for the foregoing employment opportunity. You further agree that you have represented information about yourself accurately and have not affirmatively misrepresented your qualifications. You also agree to maintain as confidential, to the fullest extent permitted by law, any information you learn from Vaco by Highspring about the position and you will limit disclosure of information about the position only to the extent necessary to perform any obligations in furtherance of your application. In exchange, Vaco by Highspring agrees to exercise reasonable efforts to represent you through all solicitation, job screening and resume dispersal.

For residents of Ontario, Canada: Based on Highspring’s discussions with its Client, Highspring’s understanding is that this position for employment is a current vacancy (either through Highspring as a contractor or with the client directly).

Privacy Notice

Vaco by Highspring and its parents, affiliates, and subsidiaries (“we,” “our,” or “Vaco by Highspring”) respects your privacy and are committed to providing transparent notice of our policies.

• California residents may access Vaco by Highspring HR Notice at Collection for California Applicants and Employees here.
• Virginia residents may access our state specific policies here.
• Residents of all other states may access our policies here.
• Canadian residents may access our policies in English here and in French here.
• Residents of countries governed by GDPR may access our policies here.

Additionally, submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. More details about Vaco by Highspring’s use of AI can be found here (https://www.highspring.com/ai-use-notices/). Further assessment of candidates beyond this initial phase will be conducted by recruiters and hiring managers. Vaco by Highspring does not know and cannot opine on if its client’s use of AI products in hiring.

Pay Transparency Notice

Determining compensation for this role (and others) at Vaco by Highspring depends upon a wide array of factors including but not limited to:

• the individual’s skill sets, experience and training;
• licensure and certification requirements;
• office location and other geographic considerations;
• other business and organizational needs.

With that said, as required by local law, Vaco by Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses.