Upland Qvidian Customer Roadshow Chicago Welcome You are

Upland Qvidian Customer Roadshow Chicago

Welcome

You are in good company #Qvidian. Roadshow

Agenda Time Topic Room 8: 00 -9: 00 AM Registration & Breakfast Wright-Yeager-Davis Room 9: 00 -9: 45 AM Upland Qvidian Update International Ballroom 9: 45 -10: 30 AM Qvidian Product Roadmap International Ballroom 10: 30 -11: 00 AM Break 11: 00 -11: 45 AM Customer Story | Panduit • Lisa Grabowski and Diane Nossem, Global Proposal Team “And Now for Something Completely Different” International Ballroom 11: 45 -12: 45 PM Networking lunch Wright-Yeager-Davis Room 12: 45 -1: 45 PM International Ballroom Featured Speaker | Metre Consulting • Robin Davis, President & Founder “It’s Not Rocket Surgery! Proving Your Worth with Basic Life Skills”

Agenda Time Topic 1: 45 -2: 00 PM Break 2: 00 -2: 45 PM Breakout Sessions (Choose One) • #1 | Review of Latest Qvidian Releases • #2 | Automating Security Questionnaires, DDQs and More Break • #1 | International Ballroom • #2 | Lindbergh 3: 00 -3: 45 PM Breakout Sessions (Choose One) • #1 | Review of Latest Qvidian Releases • #2 | Automating Security Questionnaires, DDQs and More • #1 | International Ballroom • #2 | Lindbergh 3: 45 -4: 00 PM Break 4: 00 -4: 45 PM Customer Story | Deluxe • Patrick Houghton-Brown, Proposal Specialist “First Steps to Get Started with Automation Today” International Ballroom 4: 45 -5: 00 PM Closing Remarks International Ballroom 5: 00 -6: 00 PM Qvidian Cocktail Reception Wright-Yeager-Davis Room 2: 45 -3: 00 PM Room

Upland Overview

Upland Software at a Glance Enterprise Work Management Cloud Software UPLD Russell 2000 Index Customer-focused, growing via M&A 450 k+ 14 Global Users Saa. S Applications Headquarters Austin, Texas Started 2012 30+ Industry Solutions Source: Company information and management (1) Based on the mid-point of our guidance range for the year ending December 31, 2018 as disclosed in the May 9, 2018 Form 8 -K, plus Q 1 gross pro forma revenue from the Inter. FAX acquisition. (2) Year-over-year recurring revenue growth based on the mid-point of our guidance range for the quarter ending 6/30/2018 as disclosed in the May 9, 2018 Form 8 -K. Project and IT Management Workflow Automation Digital Engagement 4, 000+ 100% Customers & Growing Customer Success Commitment $138 MM 60% Revenue Growth (1) (2)

Upland Product Family: Overview Project & IT Management Workflow Automation Digital Engagement Com. Sci Eclipse PPM Power. Steering Right. Answers Tenrox Accu. Route File. Bound Inter. FAX Qvidian RO Innovation Ultriva Clickability Lead. Lander Mobile Messaging Right. Answers

Upland Product Families: Use Cases Project & IT Management Workflow Automation Digital Engagement Project & Portfolio Management RFP & Sales Proposal Automation Customer Reference Automation Security & Due Diligence Questionnaires Document, Forms, & Process Automation Accounts Payable/Receivable Automation Human Resources Automation Healthcare Records Management Contract Process Automation Education Workflow Automation Government Document Management Secure Document Capture, Fax, & Distribution Enterprise-class Cloud Fax Platform Electronic Kanban Collaborative Supply Portal Application-to-Person Mobile Messaging Risk Management Lean Six Sigma/ Process Excellence New Product Development PPM Professional Services Automation (PSA) Knowledge Management (KM) for IT Support IT Governance IT Cost Management Time & Expense Management Mobile & Text Marketing Web Content Management Website Visitor Analytics & Reporting Customer Engagement Optimization Knowledge Management (KM) for Customer Service

Upland Acquires RO Innovation

Facts 90 % 9 of the world’s 10 largest software companies use RO Innovation’s Saa. S platform 65 % Historically 65% of customers are Referrals 35 % 35% of the 80 largest US technology companies utilize the RO Innovation Platform

RO Enablement Platform Quest’s

Sample of RO Customers

Upland’s Sales Enablement Vision Read Sean Nathaniel’s blog post here: bit. ly/Upland. ROblog

Qvidian Updates

Qvidian Acceleration Powered By Upland + Rapid deployment to AWS leveraging Upland experience and expanded operations resources + 30% increase in development and UX resources to deliver UI and UX improvements in 2018 + Leverage portfolio of proven technology to add best in class capabilities to the Qvidian solution 17 | Company Confidential © 2018 Upland Software, Inc.

Upland Qvidian Organizational Update + Tony De. Lollis – Sr Director of Engineering 18 | Company Confidential + Dan Montoya – Director Professional Services and Support © 2018 Upland Software, Inc.

AWS Migration Update Key Facts Key Benefits + Migration started: Feb 22 + Migrated to date: 898 clients + Data hosted in AWS: 3. 5 TB + Migrations happening through August + Faster platform + Built from the ground up + Improved database architecture + Updated disaster recovery (DR) + Superior environment monitoring + Future-proofed for scalability + Continued commitment to security process, procedures and controls 19 | Company Confidential © 2018 Upland Software, Inc.

Qvidian and You | Partnered for Success Innovation Integration Investment • RFPs in Word and Excel • Proactive sales proposals • Content management & compliance • SOWs • Security questionnaires • DDQs • PPTs • CRM • Content stores • Configure, price, quote solutions • • Continuous Improvement Stability and Performance Development expansion UI/UX Partnerships Thought leadership Customer success New hosting infrastructure

Customer Success

One unified operating model sets the foundation for customer success. GOAL High-Touch Customer Success Program Expert Professional Services 100% CUSTOMER SUCCESS (Value + Experience) Customer-Driven Innovation Exceptional Global Support 22 | Company Confidential Quality-Focused R&D Enterprise Cloud Platform © 2018 Upland Software, Inc. MEASUREMENT Net Promoter Score Financial Strength Customer Relationship Depth Customer. Defined Value Annual Employee Survey

Customer Success Program 100% Customer Success Quarterly Virtual User Conferences Net Promoter Score Onboard 23 | Company Confidential Premier Success Plans Customer Success Manager or Representative Adopt Product Feedback Loop Optimize © 2018 Upland Software, Inc. Onboarding and Training Expand Executive Outreach

Customer Success Programs Role of the customer success manager + Your Customer Success Manager + Quarterly Business Reviews (QBRs) Cadence of touchpoints; QBRs, pulse checks + Pulse checks Plug webinars – adoption series + Your champion for driving adoption & best practices + Escalations Next VUC – September 13 th, 2018 + Adoption Webinar Series + “Responding to RFPs: Workflow & Automation” + by Andy Jeffs, Qvidian + July – available now on Upland Qvidian Community + “Content Management Best Practices” + September + Next Virtual User Conference (VUC) 24 | Company Confidential + September 13 th, 2018 © 2018 Upland Software, Inc.

Net Promoter Score Survey was sent August 7 “How likely is it that you would recommend Upland Software to a friend or colleague? ” + Survey runs 2 x per year + We read every comment + We prioritize product roadmaps based on this feedback + The survey ensures there is alignment between our delivery your success goals

Services Update

University Training RFP Management On-Demand Foundations Online Guided Learning (OGL) or Virtual Instructor-Led Training (VILT) Advanced Content Management Virtual Instructor-Led Training (VILT)

Qvidian University Roadmap + Current Offerings • Qvidian Foundations (VILT and OGL) • Advanced Content Management (VILT) • Analytics Standard Dashboards • RFP Management On Demand + New Courses - Q 3 of 2018 • Advanced Architecture (OGL) + New Courses - Q 4 of 2018 • Moving from Library to Projects (VILT) • Content Management for RFPs (VILT) 28 | Company Confidential © 2018 Upland Software, Inc.

New Services Packages + Consulting Service Package • Two seats to Adv. Content Management, document type refresh, style template refresh, library audit, 8 hours of remote consulting/training + New Document Type Service Package • Half-day remote strategy session, 1 document type, prepare, load and associate 250 pieces of content, create and deliver custom training to support the new document type, 4 hours of remote consulting 29 | Company Confidential © 2018 Upland Software, Inc.

New Services Packages + Training Service Package • 2 seats to Qvidian Foundations, 2 seats to Adv. Content Management, 4 seats to RFP Management, 6 hours of remote hourly training + Training and Consulting Service Package – Lite • 2 seats to Foundations Online Guided Learning, 2 seats to Adv. Content Management, 4 hours of remote consulting/training 30 | Company Confidential © 2018 Upland Software, Inc.

Poll Question 31 | Company Confidential © 2018 Upland Software, Inc.

Best Practices • In-Product Help • Search: Best Practice • Open Q&A • Every Tuesday and Thursday • Community • Newsletter

Product Roadmap Update

Wrap Up

To our speakers, THANK YOU! Lisa Grabowski & Diane Nossem of Panduit Robin Davis of Metre Consulting Patrick Houghton-Brown of Deluxe

Let's Continue the Conversation. . . + Stay tuned for our post-Roadshow email • Review our Boston Roadshow event by responding to our brief survey • Download some of the presentations from today’s event to use what you’ve learned + Keep tabs with us online • Qvidian. com | access Blogs, e. Books, Case Studies, and Thought Leadership pieces • Follow us on Twitter @Upland. Qvidian, and find us on Linked. In for regular updates • Check out the Qvidian Community 36 | Company Confidential © 2018 Upland Software, Inc.

On the road… Did your colleagues miss out today? Don’t worry, there are two more stops on the 2018 tour. Spread the word! + Orlando: September 19 (University Training September 20) + Montreal: October 3

Qvidian University | Exclusive Roadshow Offer + 20% off any University course + Coupon code “Roadshow 2018” + Register here: https: //uplandsoftware. com/qvidia n/qvidian-resources/university/ 38 | Company Confidential © 2018 Upland Software, Inc.

Thought Leadership + Qvidian partnering with Strategic Proposals to develop and deliver • Best practice webinar series • Whitepapers and Blog posts • Value-added services + Stay tuned for dates and offers 39 | Company Confidential © 2018 Upland Software, Inc.

University Training Day – Logistics + Update: Check-in outside International Ballrooms Foyer + Breakfast at 8: 00 am + Training begins at 8: 30 am • Hands-on training, bring your laptop + Two sessions • RFP (Sheryl Drasler) - Wright-Yeager Ballroom • Content Management (Leah Hooper) - Hughes Ballroom + Lunch at 12: 00 pm - Davis Ballroom + Training restarts at 1: 00 pm • Workshop style training + Concludes at 3: 30 pm 40 | Company Confidential © 2018 Upland Software, Inc.

Thank You! Let’s head next door for some beverages, hors d’oeuvres, and conversation!