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Sidetrade

AI-powered SaaS optimizing order-to-cash

Sales Manager - NA SMB

Account ExecutiveUpdated on Nov 10
Full-timeCalgary, AB, CanadaNo salary listed

About the Job

Requirements

  • At least 3 years of experience in a sales leadership role covering full sales cycles.
  • A proven track record of success selling SaaS solutions, ideally in B2B financial software or Order-to-Cash.
  • Demonstrated success building and scaling new-business sales teams.
  • Strong experience selling to C-suite and senior finance stakeholders, including CFOs, Finance Directors, and Credit Managers.
  • A consistent history of meeting or exceeding revenue targets.
  • Experience executing defined, repeatable sales methodologies.
  • Ability to operate effectively in a fast-paced, high-growth environment.

Responsibilities

  • Define and implement sales strategies across North America and key verticals.
  • Own regional revenue targets, pipeline health, and forecast accuracy.
  • Manage the full sales cycle from qualified meetings through long-term customer acquisition.
  • Drive repeatable, scalable sales motions aligned to SMB buying behavior in the Order-to-Cash market.
  • Partner with Marketing on demand generation, campaigns, and pipeline acceleration.
  • Recruit, onboard, coach, and retain a high-performing sales team of Account Executives and Business Development Representatives.
  • Provide ongoing training, deal coaching, and performance management.
  • Establish clear expectations, key performance indicators, and accountability across the team.
  • Foster a sales culture focused on collaboration, execution, and customer value.
  • Own weekly and monthly sales forecasting and pipeline reporting.
  • Drive strong customer relationship management discipline and data accuracy.
  • Implement and continuously improve sales processes, playbooks, and methodologies.
  • Use data and insights to identify trends, risks, and growth opportunities.
  • Maintain a strong understanding of the SMB finance, accounts receivable, and AI Order-to-Cash landscape in North America.
  • Stay up to date on industry trends, competitors, and best practices.
  • Build trusted, collaborative relationships with Product, Customer Success, Partnerships, and Marketing.
  • Act as the voice of the customer, feeding insights back into product and go-to-market strategy.

Desired Qualifications

  • Entrepreneurial mindset with a passion for building, testing, and scaling.
  • Self-starter with strong ownership mentality and bias for action.
  • Ideally, experience selling SaaS solutions in B2B financial software or Order-to-Cash.

About the Company

Sidetrade

AI-powered SaaS optimizing order-to-cash

Sidetrade provides an AI-powered SaaS platform for optimizing the order-to-cash (O2C) process, called Augmented Cash. It uses its proprietary AI assistant, Aimie, trained on a large data lake of B2B payment transactions, to forecast customer payment behavior, recommend collection strategies, automate dunning, resolve invoice disputes, and improve cash flow. The product is delivered as a subscription SaaS and targets finance departments in large, international companies across multiple industries. Sidetrade differentiates itself with its data-driven Aimie assistant, its global reach (over 85 countries), and recognition as a Gartner Leader in Invoice-to-Cash. The company's goal is to help businesses reduce payment delays, manage credit risk, and accelerate cash collection by providing actionable insights and automated workflows within the O2C cycle.

Company size
201-500
Company stage
IPO
Headquarters
Boulogne-Billancourt, France
Founded
2000

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