Windward Software Systems Inc.

Role Description This job posting is for a remote, 8-week full-time AI Product Intern role at Windward Software Systems Inc. The intern will work with the Product Team to help build AI agents that gather, analyze, and prioritize product information, while collaborating with Product, Engineering, and Customer Success. It’s aimed at someone curious, detail-oriented, and excited to gain hands-on experience in AI development. As the AI Product Intern, you’ll gain hands-on experience in every stage of agent development and product intelligence, including: - Product information gathering: Designing and implementing agents to collect, organize, and synthesize data from various sources. - Information analysis and understanding: Using AI techniques to process, interpret, and extract actionable insights from product data. - Gap identification: Building tools and agents to detect gaps in product knowledge, documentation, or customer feedback. - Prioritization and reporting: Developing systems to help prioritize product improvements and generate actionable reports for stakeholders. This is not an internship where you’re on the sidelines—expect to actively participate in meetings, share your ideas for agent designs and product intelligence, and collaborate directly with the Product, Engineering, and Customer Success teams to drive innovation. You’ll learn new AI techniques and skills that will set your career up for success. If you’re driven, inquisitive, detail-oriented (accuracy matters!), and excited to launch your AI development career, apply today and tell us why you’d be a great fit. Bonus points if you already have experience using AI tools to advance information gathering and product intelligence. This internship is remote, for 40 hours a week, for 8 weeks. Qualifications - Curious and detail-oriented mindset. - Passion for technology and AI development. - Experience using AI tools to advance information gathering and product intelligence (bonus). Requirements - Availability for 40 hours a week for 8 weeks. - Student (Fixed Term) (Trainee). Benefits - Salary Range: $20-$34/hour. - Opportunities for professional growth and development. Company Description We value our talented employees, and whenever possible strive to help one of our associates grow professionally before recruiting new talent to our open positions. If you think the open position you see is right for you, we encourage you to apply! Our people make all the difference in our success.

Role Description We are looking for an Intermediate Sales Development Representative (SDR) to help drive new customer growth for our business management software solutions. This role focuses on identifying, engaging, and qualifying prospective customers, while working closely with Marketing and Business Development to support the full sales cycle. We are looking for someone who is skilled at engaging in quality sales and prospecting conversations, modern prospecting techniques, and thoughtful qualification, supported by the effective use of technology and AI enabled tools. Qualifications - 2–3 years of experience in a B2B SDR, BDR, or similar sales development role - Experience working with SMB or mid‑market prospects and customers - Strong communication, discovery, and qualification skills - Comfort using AI‑enabled sales tools to support research, outreach, and follow‑up - Experience using a CRM system (HubSpot, Salesforce, or similar) Requirements - Identify and engage prospective customers within defined industries and ideal customer profiles, including prospecting list development and hygiene - Execute targeted outbound outreach using phone, email, LinkedIn, and modern sales tools - Leverage AI‑assisted tools to research accounts, personalize messaging, and prioritize outreach - Respond within established service levels to inbound inquiries and marketing‑generated leads - Conduct discovery conversations to understand prospect needs, challenges, and existing systems - Identify decision‑makers, buying processes, and timelines - Use AI‑supported insights (e.g., call summaries, account research, messaging optimization) to improve discovery quality - Qualify or disqualify opportunities based on fit, readiness, and long‑term value alignment - Schedule qualified discovery or demo meetings with a Senior Business Developer - Provide thorough and accurate handoff notes, including business context, pain points, and stakeholders - Collaborate with sales and marketing leadership to continuously refine targeting, messaging, and qualification standards - Maintain accurate CRM records for all activities, conversations, and lead status - Use AI‑enabled CRM features responsibly to improve efficiency, data quality, and follow‑through - Follow defined sales development and qualification processes Benefits - Consistently generating high‑quality, sales‑ready opportunities - Strong alignment with the sales and marketing teams on opportunity quality - Professional, consultative conversations with prospective customers - Effective and ethical use of AI to enhance productivity and buyer experience - Accurate CRM records and reliable follow‑through

Job Summary: Windward Software is hiring a summer Marketing Intern to support B2B marketing initiatives across research, content creation, and digital publishing. In this hands-on role, you’ll help produce marketing assets, analyze competitors, and assist with website updates and marketing operations using tools like HubSpot, Adobe Creative Suite and other AI assisted marketing and content creation tools. This internship is ideal for a self-starter eager to build practical experience and a portfolio of real-world work. Job Description: Marketing Intern (Summer – Fixed Term) Company: Windward Software Location: Remote (North America preferred) Term: Summer Internship (Fixed term) About the Role Windward Software is seeking a motivated and detail-oriented Marketing Intern to support our Marketing team over the summer. This is a ‑hands-on role designed to provide ‑real-world‑ experience across B2B software marketing, including market research, content creation, digital publishing, and marketing operations. The ideal candidate is eager to learn, comfortable working independently, and interested in gaining experience with modern marketing tools such as HubSpot, Canva, and AI assisted‑ content tools. Key Responsibilities Market & Competitive Research - Conduct market research to support marketing initiatives and campaigns - Gather and compile competitive pricing analysis - Analyze competitor social media presence, including: - Types of posts and content themes - Media formats used (video, graphics, text) - Engagement levels and follower growth - Compile competitive feature comparisons as needed Content Creation - Write and assist with: - Blog posts - Targeted email content - Social media post drafts - Support the development of marketing collateral such as: - One-‑pagers - Campaign assets - Sales enablement‑ materials Content Publishing & Design - Design content layouts using tools such as Canva or Adobe Creative Suite, when applicable - Perform light video editing using Adobe Express, Premiere, or equivalent tools - Prepare approved content for website publishing, including: - Page template setup - Text formatting in the HubSpot editor - Adding CTAs, forms, images, and metadata for SEO - Support content review and approval workflows Events & Marketing Operations Support - Assist with marketing support for events and tradeshows as needed - Perform data integrity audits and data scrubbing within marketing systems Qualifications & Skills - Basic understanding of SEO principles - Basic understanding of web image formats and optimization - Strong writing skills with the ability to conceive, draft, proofread, and edit content efficiently - Excellent attention to detail and strong grammatical skills - Ability to develop content that requires little or no editing - Strong organizational skills with the ability to manage multiple projects and deadlines - Comfortable working independently while collaborating within a team environment - Experience routing work for feedback and approvals - B2B writing experience is an asset, but not required - Interest in software, technology, or digital marketing is a plus Technical Requirements - Experience or familiarity with: - HubSpot Content Management System (preferred) - Canva or Adobe Creative Suite - AI‑assisted marketing or content tools - Basic understanding of: - Image editing and optimization tools - Content management systems What You’ll Gain - Hands‑on experience in B2B software marketing - Exposure to real marketing campaigns, tools, and workflows - Practical experience with HubSpot, content publishing, and marketing operations - Mentorship from an experienced marketing team - Portfolio ready‑ work across content, research, and digital marketing Worker Type: Student (Fixed Term) (Trainee) Number of Openings Available: 1