CAI Software, LLC

Financial Planning and Analysis

• Serve as a trusted right hand to the CEO and CFO, anticipating needs, removing friction, and protecting executive time and focus
• Manage complex, ever-changing CEO and CFO calendars across multiple time zones; resolve conflicts with sound judgment on priority and trade-offs
• Schedule and coordinate internal and external meetings, including leadership team, customer, partner, sponsor, and board-level interactions; prepare agendas, pre-reads, and logistics so each meeting starts on time and ends with clear outcomes
• Act as gatekeeper for incoming communications, requests, document signing, and meeting invitations; triage and align with quarterly priorities and value-creation initiatives
• Prepare, format, and proof high-quality reports, presentations, and briefing materials for internal leadership, board, sponsor, and external audiences
• Coordinate end-to-end logistics for Board of Directors and sponsor meetings — scheduling, materials assembly, distribution, dinners, and follow-up correspondence
• Partner with the CFO and Finance team on board books, quarterly reporting packages, and committee materials; maintain board portal and secure data-room organization
• Support the CFO with the rhythm of the financial calendar — month-end and quarter-end close, audit, budget, lender reporting, tax, and insurance timelines
• Support a high-tempo M&A and integration agenda by coordinating diligence calls, management presentations, site visits, and signing/closing logistics
• Plan and manage detailed domestic and international travel for the CEO and CFO, including flights, ground transportation, accommodations, visas, and resilient backup plans for disruptions; reconcile expenses promptly and accurately
• Plan and execute corporate events, leadership offsites, sponsor visits, customer dinners, town halls, and team meetings; manage venue selection, vendors, contracts, and budget tracking
• Track action items, decisions, and follow-ups across executive forums and ensure timely closure with accountable owners
• Support general office administration in the executive suite; maintain organized filing systems, contract repositories, and executive records, both physical and digital
• Handle highly confidential information with the highest level of discretion

Executive Assistant – CEO, CFO

Compliance

• Own the recovery pipeline for lapsed and expired renewals, with a primary focus on contracts that went past due in the prior fiscal year
• Research account history, contract terms, and prior engagement activity to build an informed outreach strategy for each lapsed account
• Execute multi-channel outreach campaigns (phone, email, escalation) to re-engage customers and drive contract reinstatement or back-dated renewal agreements
• Negotiate renewal terms for lapsed contracts, including handling objections around gaps in coverage, retroactive pricing, and reinstatement fees
• Collaborate with Legal, Deals Desk, and Finance to structure recovery agreements that are commercially sound and executable
• Track and report on recovery pipeline status, conversion rates, and recovered ARR on a weekly basis
• Partner with Sales and Customer Success to identify accounts where software usage exceeds licensed entitlements
• Analyze deployment data, license records, and usage reports to build compliance cases with clear, defensible documentation
• Lead compliance outreach conversations with customers, presenting findings professionally and guiding accounts toward compliant licensing and true-up agreements
• Develop and refine compliance playbooks, escalation workflows, and communication templates in partnership with leadership
• Coordinate with Legal on escalation strategy for non-responsive accounts or disputes related to compliance findings
• Maintain accurate records of all customer interactions and pipeline activity in internal tracking systems
• Provide regular status updates and forecasts to Renewals leadership
• Cross-functionally collaborate with internal stakeholders to deliver competitive solutions and resolve complex account issues
• Contribute to the development of policies, processes, and best practices for the renewals and compliance function

Software Renewals, License Compliance Specialist

Account Executive

• We are seeking a driven, results-oriented Account Executive - SMB to support the next phase of growth within CAI Software.
• This role is responsible for net-new logo acquisition, as well as, expansion of existing Small and Mid-size customers, working closely with Customer Success.
• Own and consistently meet or exceed an assigned revenue quota for the North America territory, with a proven track record of closing 6- and 7-figure deals.
• Execute a territory strategy focused on net-new logo acquisition and land-and-expand growth within strategic enterprise accounts.
• Operate as a true hunter, generating a significant portion of pipeline through outbound prospecting, executive outreach, and targeted account-based strategies, while effectively managing inbound demand.
• Lead and manage complex, multi-threaded SMB sales cycles, navigating procurement, legal, security, and executive decision-makers.
• Create urgency and momentum by tying solutions to measurable business outcomes, including operational efficiency, compliance, scalability, and ROI.
• Build, qualify, and maintain a robust, self-sourced pipeline aligned to enterprise growth targets.
• Forecast accurately and consistently, managing opportunities through defined sales stages with disciplined deal inspection.
• Drive deal progression by establishing clear next steps, mutual action plans, and executive alignment.
• Lead land-and-expand strategies within SMB accounts, identifying opportunities for additional sites, locations, use cases, and cross-sell/upsell expansion.
• Maintain executive relationships to unlock incremental budget and expansion opportunities over time.
• Work cross-functionally with Marketing, Product, Services, and Customer Success to drive coordinated enterprise account strategies.
• Provide structured feedback from the field to influence product roadmap, messaging, and go-to-market strategy.
• Engage and influence stakeholders across operations, manufacturing, IT, quality, procurement, and executive leadership.
• Lead high-impact discovery sessions, executive presentations, demos, and onsite meetings as required.
• Travel to customer locations to support deal progression, executive alignment, and long-term relationship building.

Account Executive – SMB

• Drive Revenue & Territory Growth
• Own and execute the full sales cycle, from prospecting and discovery through proposal development, ROI presentations, negotiation, and close.
• Develop and manage a strong pipeline using Salesforce, providing accurate forecasts and clear visibility to leadership.
• Achieve monthly, quarterly, and annual revenue targets while managing discount levels and operating within budget guidelines.
• Expand market share and strengthen CAI’s presence within the commercial print sector.
• Lead Complex Sales Engagements
• Navigate complex enterprise sales cycles involving internal cross-functional teams including Sales, Product Management, Professional Services, Finance, Legal, and Executive Leadership.
• Position CAI solutions strategically to senior leadership teams within commercial print organizations.
• Build Strategic Relationships
• Engage regularly with prospects and customers through onsite visits, virtual meetings, webinars, and industry events.
• Collaborate with other CAI sales teams to drive cross-selling initiatives.
• Partner with Product, Engineering, and Marketing teams to align solutions with market demands.
• Represent the Brand
• Attend and actively participate in trade shows, open houses, and company-sponsored events.
• Maintain deep knowledge of CAI products, competitive positioning, and industry trends.
• Act as a market ambassador, positioning CAI as a leader in the commercial print space.

Account Executive – Enterprise

• Own and consistently meet or exceed an assigned SMB revenue quota for the EMEA territory
• Execute a territory strategy focused on net-new logo acquisition and land-and-expand growth within strategic SMB accounts
• Operate as a true hunter, generating a significant portion of pipeline through outbound prospecting, executive outreach, and targeted account-based strategies
• Lead and manage complex, multi-threaded SMB sales cycles, navigating procurement, legal, security, and executive decision-makers
• Create urgency and momentum by tying solutions to measurable business outcomes
• Build, qualify, and maintain a robust, self-sourced pipeline aligned to SMB growth targets
• Forecast accurately and consistently, managing opportunities through defined sales stages
• Lead land-and-expand strategies within SMB accounts
• Work cross-functionally with Marketing, Product, Services, and Customer Success to drive coordinated SMB account strategies
• Engage and influence stakeholders across operations, manufacturing, IT, quality, procurement, and executive leadership

Account Executive, SMB

• Consistently exceed quarterly and annual sales targets as an individual contributor
• Own the full sales cycle, from lead qualification through contract close
• Develop and execute account strategies to drive growth across assigned territory
• Establish and maintain long-term, trusted advisor relationships with new and existing clients
• Partner with sales and marketing teams to uncover upsell and cross-sell opportunities within accounts
• Research target companies and decision-makers to generate and qualify new sales opportunities
• Deliver compelling, value-focused product demonstrations to prospective users
• Negotiate pricing, terms, and conditions within approval guidelines to maximize deal value
• Leverage Salesforce.com and other sales tools to provide accurate sales forecasts and pipeline reports to leadership

Inside Sales Representative – SMB

• Drive Revenue & Territory Growth
• Own and execute the full sales cycle, from prospecting and discovery through proposal development, ROI presentations, negotiation, and close
• Develop and manage a strong pipeline using Salesforce, providing accurate forecasts and clear visibility to leadership
• Achieve monthly, quarterly, and annual revenue targets while managing discount levels and operating within budget guidelines
• Expand market share and strengthen CAI’s presence within the commercial print sector
• Navigate complex enterprise sales cycles involving internal cross-functional teams including Sales, Product Management, Professional Services, Finance, Legal, and Executive Leadership
• Engage regularly with prospects and customers through onsite visits, virtual meetings, webinars, and industry events

Account Executive – Graphic Communications

Human Resources

• Maintain and update HR systems, databases, trackers, and shared platforms, ensuring data accuracy and compliance
• Manage relationships with third-party vendors (e.g., payroll providers, pension schemes, company cars, occupational health, benefits platforms, visa providers)
• Support onboarding and offboarding processes, including documentation and employee lifecycle administration
• Prepare employee correspondence, including contractual changes and HR letters
• Manage the EMEA HR inbox, ensuring timely and accurate responses, appropriate prioritisation, and escalation where required
• Coordinate and manage payroll processes across the UK, France, Germany, the Netherlands, and Belgium
• Act as the first point of contact for payroll-related queries (e.g., salary, deductions, benefits, holidays)
• Liaise with external payroll providers to ensure accurate and timely payroll delivery
• Validate payroll data, track changes, and ensure compliance with local legislation
• Provide first-line support and guidance to managers and employees on HR policies and procedures
• Assist in handling employee relations matters, including grievances, disciplinary cases, and investigations

HR Generalist

• Own and execute the full sales cycle, from prospecting and discovery through proposal development, ROI presentations, negotiation, and close
• Achieve monthly, quarterly, and annual revenue targets while managing discount levels and operating within budget guidelines
• Engage regularly with prospects and customers through onsite visits, virtual meetings, webinars, and industry events
• Build, qualify, and maintain a robust, self-sourced pipeline aligned to enterprise growth targets

• Drive customer success through strategic, consultative selling
• Lead the end-to-end SaaS sales process
• Self-source approximately 50% of total pipeline
• Build relationships with VP-level decision-makers
• Execute against the MEDDPICC qualification framework
• Lead with ShopVue MES as the primary solution

Account Executive – Discrete Manufacturing

• Responsible for net-new logo acquisition and expansion of existing Small and Mid-size customers
• Meet or exceed assigned revenue quota for the North America territory
• Execute territory strategy focused on net-new logo acquisition and land-and-expand growth
• Operate as a true hunter, generating pipeline through outbound prospecting and account-based strategies
• Lead and manage complex, multi-threaded SMB sales cycles
• Create urgency and momentum by tying solutions to measurable business outcomes
• Build, qualify, and maintain a robust, self-sourced pipeline
• Forecast accurately and consistently, managing opportunities through defined sales stages
• Lead land-and-expand strategies within SMB accounts
• Work cross-functionally with Marketing, Product, Services, and Customer Success

Executive Assistant – CEO, CFO

Software Renewals, License Compliance Specialist

Account Executive – SMB

Account Executive – Enterprise

Account Executive, SMB

Inside Sales Representative – SMB

Account Executive – Graphic Communications

HR Generalist

Account Executive – Graphic Communications

Account Executive – Discrete Manufacturing

Account Director – SMB