Role Description At Upland Software, you’ll find smart, creative teams who love working together to deliver value for our customers, and a global culture of growth and possibility. Our operating model has always supported remote work—and as we keep growing and evolving our workplace, that won’t change. We’re passionate. We’re proactive. We take pride in our work, and we love a good challenge. Sound like you? The Sales Development organization is a critical engine for pipeline creation and go‑to‑market execution. The SDR Manager plays a pivotal leadership role, responsible for translating strategy into daily execution while developing high-performing SDR talent. This role is ideal for a leader who enjoys building systems, enforcing standards, and coaching to outcomes. The right person will influence pipeline results, improve execution quality, and help scale consistent, repeatable SDR performance across inbound and outbound motions. Qualifications - 2+ years of experience managing and coaching Sales Development or inside sales teams - Proven ability to drive pipeline through disciplined execution and accountability - Strong coaching skills with a focus on call quality, messaging, and conversion performance - Data-driven mindset with comfort analyzing dashboards, activity metrics, and funnel performance - Experience working cross-functionally with Sales, Marketing, and Revenue Operations - Excellent communication skills with the ability to set expectations clearly and directly - High ownership mentality and bias toward action Requirements - Familiarity with SDR productivity and engagement platforms (e.g., Outreach, Nooks, Sales Navigator, 6sense) - Strong Salesforce (or CRM) experience with reporting and pipeline tracking - Background in B2B SaaS or complex sales motions - Experience managing both inbound and outbound SDR motions - Ability to influence without authority and navigate change effectively Company Description Upland Software (Nasdaq: UPLD) is a leader in cloud-based tools for digital transformation. To learn more, visit www.uplandsoftware.com . Upland Software is an Equal Employment Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status or other legally protected status.

Role Description The Sales Development Representative is responsible for promoting D2L Products and Services, establishing customer relationships, and providing qualified, motivated leads to the Sales teams. As a key member of the sales team, the successful candidate will have in-depth knowledge of the company’s solutions, competition, and a keen interest in the eLearning industry. The primary market focus is the education and corporate sectors. We are looking for an energetic, polished individual with exceptional communication skills and a talent for relationship building. The successful candidate will gain expertise in accurately capturing and qualifying leads, effectively managing a sales pipeline, and achieving quarterly revenue targets. This Sales Development Representative provides a challenging career opportunity as well as career advancement within D2L. How You Will Make an Impact: - Responsible for exceeding objectives within your assigned territory - Able to understand and deliver D2L's unique value proposition and create solution vision with prospects - Actively participate in outbound calling campaigns to generate sales opportunities - Accurately capture and qualify leads gathered from trade shows, webinars, inbound calls, and other marketing initiatives - Follow-up with existing D2L contacts and develop them into sales prospects - Distribute leads and make qualified appointments for Sales Executives - Create and update lead generating emails and phone scripts - Update customer interactions through the CRM tool - Complete sales reports and present findings to executive management - Conduct market research and keep updated on product and industry knowledge, competitors, and industry knowledge - Represent D2L at occasional trade shows; some travel will be required Qualifications - 1-2+ years in a Sales Development Role - Interest in pursuing a sales career within a fast-paced, constantly changing environment - Pro-active and goal oriented with the ability to maintain consistent levels of customer activity to generate sales leads and meet quarterly objectives - Excellent written and verbal communication skills - Excellent time management skills with the ability to multi-task and organize/prioritize work independently - Strong interpersonal and customer orientation skills with the ability to influence decision makers - Demonstrated ability to work individually and collaboratively within a team environment - Previous experience in eLearning, the education sector, enterprise software and/or high tech solutions providers preferred Education Recommendations: - Degree or diploma in Business, Marketing or related Benefits - Impactful work transforming the way the world learns - Flexible work arrangements - Learning and Growth opportunities - Tuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program - 2 Paid Days off for SkillsWave-related activities like exams or final assignments - Employee wellbeing (Access to mental health services, EFAP program, financial planning and more) - Retirement planning - 2 Paid Volunteer Days - Competitive Benefits Package - Home Internet Reimbursements - Employee Referral Program - Wellness Reimbursement - Employee Recognition - Social Events - Dog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices

• Proactively source and initiate exploratory conversations about a valuable and unique product, one people are willing to take cold calls for. • Book discovery meetings that convert into qualified opportunities for Account Executives (AEs). • Qualify prospects based on established criteria and gather key sales intelligence. • Achieve and exceed monthly and quarterly goals for generating qualified opportunities to power the sales pipeline. • Maintain strong outreach activity across multiple channels: calls, emails, live chat, video meetings, and LinkedIn messages. • Identify, research, and perform personalized outreach to companies that match our Ideal Customer Profiles (ICPs). • Ensure an exceptional customer experience with natural empathy for the needs of both new prospects and existing accounts • Provide ongoing feedback on workflows, sales tools, lead quality, and marketing campaign results. • Help define and continuously improve the outbound sales motion, contributing to the foundation of our demand generation process.

Role Description Our sales pitch is working. Our ICP is responding. The gap is volume. We need consistent, high-quality outreach to keep the funnel full. The CEO is currently running sales, and we're not looking for management overhead — we're looking for a sharp, execution-focused SDR who treats pipeline-building as a craft. You'll own top-of-funnel, build outreach infrastructure, and scale prospecting using modern AI sales tools. This is not a support role. You'll have direct access to the CEO, real influence on the GTM motion, and full ownership of the outbound engine from day one. What You'll Own - Outreach & Pipeline Generation: - Build and continuously refine a multi-channel outreach engine (LinkedIn, email, phone) targeting VP/Director/C-suite buyers at mid-to-large retail chains and automotive groups. - Use AI SDR tools (Clay, Apollo, Instantly, Amplemarket, or equivalent) to automate, sequence, and personalize outreach at scale. - Maintain a healthy daily cadence of outbound touches and book qualified discovery calls for the CEO and growing sales team. - Own your pipeline metrics — contacts sourced, emails sent, reply rates, meetings booked — and optimize relentlessly. - LinkedIn & Social Selling: - Execute a LinkedIn-first strategy: targeted connection campaigns, personalized DMs, content engagement, and Sales Navigator workflows. - Identify and track buying signals (job changes, company growth, hiring activity) to prioritize outreach timing. - Support the CEO's personal LinkedIn presence with strategic engagement to amplify brand visibility. - HubSpot & CRM Ownership: - Own HubSpot hygiene — contacts, companies, sequences, and deal stages kept clean and current. - Build and maintain HubSpot sequences, workflows, and reporting dashboards that give full pipeline visibility. - Instrument the funnel so leadership can always see what's working and what's not. - Content-Led Outbound: - Leverage FrontlineIQ's case studies, ROI data, and thought leadership to personalize outreach — not spray-and-pray. - Draft compelling cold email and LinkedIn copy that speaks to the pain points of VP Sales, Regional VPs, and HR/L&D leaders in physical retail. - Identify gaps in the prospecting conversation and surface content needs (specific verticals, common objections). Qualifications - 1–3+ years in an SDR, BDR, or outbound sales role — ideally in B2B SaaS. - Demonstrated ability to self-manage: you set your own daily targets, track your own metrics, and don't need to be told to follow up. - Hands-on experience with HubSpot (or similar CRM) — you know how to build sequences, not just use them. - Comfortable using AI-powered tools to research, personalize, and scale outreach (Clay, Apollo, ChatGPT, etc.). - Strong written communication — your cold emails actually get replies. - High standards for organization: your CRM is always current, your follow-ups always happen on time. Requirements - Experience selling to retail, automotive, or multi-location enterprise businesses. - Familiarity with LinkedIn Sales Navigator and social selling techniques. - Prior experience at an early-stage startup where you had to build the process, not just follow one. - Track record of booking qualified meetings at a consistent weekly pace. What This Role Is Not - This is not a "Head of Sales" title at a startup still figuring out its pitch — we've done that work and the motion is working. - We're not looking for someone who needs significant marketing support or a full team before they can generate pipeline. - We don't need strategy — we need execution. If you're most energized by building decks and playbooks rather than running outreach, this isn't the right fit. - Autonomy is expected. If you need daily direction to know what to work on, this role will be frustrating for both of us. Compensation & Details - Base + Commission on meetings booked and deals sourced — structured to reward execution. - Equity: Options available — we want you invested in the outcome. - Reporting to: CEO. Why Join FrontlineIQ™ - You'll work directly with the CEO and have real influence on the GTM motion from day one. - Our product genuinely works — we have anchor customers, strong NPS, and measurable ROI. You'll be selling something you can believe in. - We're building a category. In-person sales is a massive, underserved market for AI coaching. - Early employees are well-positioned as we grow into Series A and beyond.