Breaking Barriers: How WISE is Transforming Women's Careers in Presales with Wendy McHenry

In this episode, Jack Cochran and Matthew James are joined by Wendy McHenry, Chair of WISE (Women in Solutions Excellence) at Presales Collective and Former Head of Global Solutions Engineering at CDATA, to discuss the critical need for supporting women in presales careers. They explore the challenges women face in a field where only 18% of solutions professionals are women, discuss unconscious bias in hiring and workplace environments, and highlight how WISE is creating support networks and career development opportunities to advance equity in the solutions field. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. This episode is sponsored by Elvance. More information at https://elvance.io/  On the Show Today Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Wendy McHenry: https://www.linkedin.com/in/wendymac98/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack WISE Chapter Information: https://www.presalescollective.com/wise  Presales Collective LinkedIn: https://www.linkedin.com/company/presalescollective  Timestamps 00:00 Welcome 04:51 Why WISE? 09:12 Being a woman in sales today 12:57 You’re not technical enough 16:16 Women leaving the profession 20:33 How is WISE helping? 27:55 What’s happening next? Key Topics Covered The Current State of Women in Presales Only 18% of solutions professionals globally are women Many women are the only woman on their SE team Higher attrition rates during layoffs disproportionately impact women Unconscious Bias and Workplace Challenges "Not technical enough" bias applied differently to women Interview panels dominated by men Social environments that may exclude women The importance of calling out bias when witnessed WISE Mission and Structure Started as an ERG at Salesforce, now part of Presales Collective Open to anyone who cares about supporting women in solutions careers Regional chapters like Women in Solutions Consulting Australia/New Zealand Company-specific chapters at organizations like Salesforce and Pegasystems Creating Change and Allyship How to be an effective ally in supporting women's careers Starting WISE chapters at your company (or expanding to broader sales/tech groups) The importance of diverse account teams and client representation Free career coaching and mentorship available through WISE council

In this episode, Jack Cochran and Matthew James are joined by Akash Ganapathi, CEO of Opine, to discuss how AI strategies differ between startups and enterprises in the presales space. They explore the myth of AI replacing SEs, the importance of specialization vs. generalization, and how AI can help presales teams manage more revenue per team member while focusing on strategic, relationship-building activities. Follow Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Akash Ganapathi: https://www.linkedin.com/in/akash-ganapathi/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Opine: https://tryopine.com/ Contact Akash directly: [email protected] Timestamps 00:00 Welcome 04:35 Why AI strategy differs for startups vs enterprises 09:27 Debunking the myth of AI replacing SEs 18:35 The human element in buying and selling 24:35 How enterprises can leverage existing knowledge bases 28:12 The paradox of considering AI for every task 32:14 Future predictions for 2026-2027 Key Topics Covered Startup vs Enterprise AI Strategy Startups benefit from generalist approaches and bottom-up experimentation Enterprises need specialized, top-down AI strategies to avoid redundancy The role of specialization vs wearing multiple hats The AI Replacement Myth Why the "AI SE" that replaces human SEs doesn't work SEs do much more than just answer technical questions The importance of relationship building and strategic thinking Current AI Limitations Context window constraints (around 1 million tokens currently) Retrieval Augmented Generation (RAG) accuracy at ~75% Why breakthrough improvements are needed for true automation The Future of Presales with AI More revenue managed per team member Shift toward hiring less experienced SEs with AI enablement Focus on strategic consulting rather than administrative tasks Practical AI Implementation Draft-and-approve workflows for deliverables Automating account research, meeting prep, and RFP responses Using AI for onboarding and knowledge enablement Mid-Market Recommendations Lean toward enterprise-style, forward-looking strategies Enable not just current team but future hires Focus on cross-organizational enablement (AEs, product, marketing)  

In this episode, Jack Cochran and Matthew James are joined by Ben Hills, Founder and CEO of Iris, to discuss how to scale presales teams effectively while avoiding burnout. They explore the difference between healthy high performance and unsustainable overwork, the role of AI in streamlining repetitive tasks like RFPs, and practical strategies for building scalable processes that enhance rather than replace human expertise. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Ben Hills: https://www.linkedin.com/in/benjaminhills/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Iris: https://heyiris.ai/ Timestamps 00:00 Welcome 04:04 Iris 05:14 Ben's background 14:29 Healthy high performance vs burnout 21:55 Common scaling mistakes and the headcount trap 29:14 Effective AI tools for presales teams 35:04 The future of AI-to-AI RFP processes 37:46 Final advice on embracing AI Key Topics Covered Understanding Burnout vs. High Performance Why burnout isn't just about hours worked The importance of connecting work to larger purpose and outcomes Creating time-bound periods of intense work with clear endpoints Scaling Without Adding Headcount The "mythical man month" problem in presales Building playbooks and processes before hiring Separating "in the business" vs "on the business" work The Rocks, Pebbles, Sand Framework Planning for big quarterly tasks (rocks) Managing predictable weekly activities (pebbles) Handling unexpected fire drills (sand) AI Tools That Actually Work RFP automation and response generation Call transcript analysis for product feedback Demo automation with synthetic data Why AI SDRs haven't lived up to the hype The Future of RFPs and AI Model Control Protocol (MCP) for AI-to-AI communication Maintaining personalization in automated processes The buyer's perspective on RFP proliferation  

In this episode, Jack Cochran and Matthew James are joined by Ben Pearce, founder of Elevated You, to discuss how technical professionals can effectively communicate with senior executives. They explore the critical differences between speaking to technical stakeholders versus C-suite leaders, covering everything from preparation strategies to delivery techniques. Ben shares practical frameworks for being relevant rather than just expert, emphasizing the importance of focusing on "what" and "why" instead of "how" when presenting to senior leaders. Thank you to Storylane for sponsoring this episode. Find out more about Storylane and how to build killer demos in 2 minutes at https://storylane.io To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Ben Pearce:https://www.linkedin.com/in/benpthoughts/ Links and Resources Mentioned Presales Collective Slack: https://www.presalescollective.com/slack Elevated You: https://www.elevatedyou.live/psc Tech World Human Skills Podcast: https://www.elevatedyou.live/twhs  Timestamps 00:00 Welcome 05:18 Why speaking to senior leaders is different 12:49 Being relevant vs. being an expert 16:19 Mastering delivery under pressure 25:04 Reading the room and course-correcting 32:53 De-risking and the human element Key Topics Covered The Technical Expert's Dilemma How technical expertise can become a curse when speaking to executives Moving from demonstrating knowledge to demonstrating relevance The Three-Part Framework for Executive Communication Relevance: Understanding what matters to your specific audience Compelling Content: Creating materials that speak to their priorities Excellent Delivery: Performing under pressure with confidence Preparation Strategies Mapping out personas and industries for reusable content The importance of team collaboration in content creation Practice vs. preparation: Why both are essential Reading the Room Starting with curiosity and mini-discovery Mirroring language and adapting on the fly Course-correcting based on real-time feedback The Punchline Problem Why building up to a big reveal doesn't work with executives Leading with impact: "Hitting them between the eyes" Getting to value within the first 90 seconds Risk Management and Trust Building Understanding that you represent organizational risk The "never get fired for buying IBM" mentality How human skills differentiate in an AI-driven world Building confidence through listening and problem-solving  

In this episode, Matthew James and Timmy Hendrickson are joined by Nalin Senthamil, Founder and CEO of Storylane, to discuss the future of pre-sales and AI driving influence beyond pipeline. They explore how demo automation is transforming the self-serve buyer experience, the changing role of solutions engineers, and how AI can create 10X impact in pre-sales workflows. Nalin shares insights on leveraging AI for demo personalization, managing complex product integrations, and why the traditional discovery call may be dying. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Timmy Hendrickson: https://www.linkedin.com/in/timmyhendrickson/ Connect with Nalin Senthamil: https://www.linkedin.com/in/nalinpradeep/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Storylane: https://www.storylane.io/ Timestamps 00:04 Welcome 01:08 Nalin's background and founding Storylane 03:08 What does a self-serve buyer experience look like? 08:18 How AI has changed presales 13:40 Training AI agents to answer technical questions 17:02 AI testing customer scenario 19:28 Overlooked use cases for demo automation 26:30 One workflow where AI can create 10X impact today Key Topics Covered The Death of Discovery Calls Why buyers are coming to conversations already educated How self-serve experiences span the entire buying journey The role of AI sales agents in initial discovery The Four Categories of SE Work Relationship building and strategic solutioning Demo delivery and POC management Administrative tasks and CRM updates Knowledge sharing and product insights AI as an SE Sidekick Demo preparation and tailoring automation Administrative task reduction Strategic thinking enhancement rather than replacement Demo Automation Use Cases Supporting different AE to SE ratios Managing complex product integrations Upsell and expansion opportunities Micro-demos for specific features Training AI for Technical Questions Leveraging tribal knowledge from Slack, Google Drive, and call recordings Importance of data quality and curation Automatic ingestion of organizational knowledge The Future of Pre-Sales AI enabling faster iteration and personalization Strategic partnership between CS and pre-sales for upsells The evolution from technical support to strategic advisory roles  

In this second part of our conversation with Raphael Joseph, former SE turned recruiter and founder of Brando Tech, Jack Cochran and Matthew James dive deep into why traditional job hunting methods no longer work in today's market. Raphael shares strategic insights on how SEs should approach job searching in 2025, treating themselves as products and leveraging their natural skills to navigate the competitive landscape. IMPORTANT: This is Part 2 of a two-part series. Make sure to listen to Part 1 first for the complete discussion on personal branding and LinkedIn optimization. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Raphael Joseph: https://www.linkedin.com/in/raphael-joseph-23044150/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Episode Sponsor: Opine - https://tryopine.com Timestamps 00:00 Welcome 04:42 What is "classic job hunting" and why it's dead 11:52 How to get on recruiters' radar 13:33 Starting your job search the right way 21:04 Treating job hunting like account management 27:23 Interview process changes and AI requirements 30:30 Why it's not a numbers game anymore Key Topics Covered The Death of Classic Job Hunting Why sending CVs to job postings no longer works How companies receive hundreds of applications they can't process The cycle of posting jobs, failing to hire, then using recruiters Why your application often goes unread The New Digital Job Hunting Approach Treating yourself as a product you're selling Building warm leads with hiring managers Using SE skills for job hunting: research, discovery, and value proposition The importance of targeted, high-touch approaches over spray-and-pray Working with Recruiters Effectively Why good recruiters provide 1-in-3 odds vs 1-in-300 direct applications How recruiters can prep you with insider knowledge The value of having internal champions in the hiring process Market Dynamics in 2025 Why it's now an employer's market The shift from growth-at-all-costs to profitability focus How COVID overhiring led to current oversupply of candidates AI's impact on hiring decisions and productivity expectations Interview Strategy in the Current Market Companies' increased specificity in requirements Why "must-haves" are truly must-haves now The importance of AI literacy and demonstrable skills How to address gaps in your experience strategically Leveraging SE Skills for Job Hunting Using research abilities to identify opportunities Applying discovery skills to understand company needs Creating value propositions for yourself as a candidate Avoiding the same mistakes SEs coach AEs to avoid  

In this episode, Jack Cochran and Matthew James are joined by Raphael Joseph to discuss the critical importance of building a strong LinkedIn profile for PreSales professionals. They explore how the platform has evolved as a powerful career tool, especially in today's competitive job market. Raphael shares practical tips on crafting a professional presence that highlights your unique value proposition, explains the impact of consistent engagement, and offers advice on creating authentic content that resonates with hiring managers. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Raphael Joseph: https://www.linkedin.com/in/raphael-joseph-23044150/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Sponsor: Opine - https://tryopine.com Timestamps 00:00 Welcome and introduction to LinkedIn's evolution 01:50 Sponsor: Opine 03:06 Raphael's background and career journey 10:46 Why you should build your LinkedIn profile before you need it 21:11 Focusing on your ideal customer profile (ICP) 25:21 Engagement strategies: connecting, commenting, and posting 33:49 Overcoming nervousness about posting Key Topics Covered LinkedIn Profile Optimization Using your banner as prime real estate to showcase your unique value Crafting a clear headline that highlights your specialization Writing descriptions that focus on the value you provide The importance of professional photos and consistent branding Strategic Profile Positioning Reverse-engineering your profile based on your target roles Focusing on 3-4 key specializations rather than listing everything Using industry-standard job titles even if your company uses different terminology Making it easy for recruiters to find you through targeted keywords Building Meaningful Connections Connecting with 100-200 potential hiring managers weekly Engaging with their content through thoughtful comments and questions Creating a network before you need it for job searching Leveraging connections for opportunities when transitions occur Content Creation Strategy Starting with comments before moving to creating original posts Sharing authentic experiences from customer interactions Finding your niche audience within the PreSales community Focusing on consistency rather than viral metrics The Changing Job Market How market conditions have shifted from candidate-focused to employer-focused Why specificity now trumps broadness in skills presentation Standing out in a competitive environment through specialization Using LinkedIn as your primary job search tool rather than traditional resumes  

In this episode, Jack Cochran and Matthew James are joined by Karthik Krishna, Manager of Solutions Engineering at Freshworks and Presales Collective's Regional Community Leader for Chennai. They explore how Solutions Engineers can gain strategic influence in deal cycles beyond just giving demos and answering technical questions. Episode Highlights Karthik shares his journey from developer to pre-sales professional The evolution from "demo-giver" to strategic partner in deal cycles How SEs can co-own opportunities with Account Executives Navigating tough conversations when deals aren't a good technical fit Building credibility to increase your strategic influence Leveraging customer success and implementation teams for deal strategy About Our Guest Karthik Krishna is a Manager of Solutions Engineering at Freshworks, where he has built and coached distributed teams of SEs across companies of all sizes. He also serves as the Presales Collective Regional Community Leader for Chennai, recently hosting an event with over 60 SEs in attendance. Follow the Hosts and Guest Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Karthik Krishna: https://www.linkedin.com/in/karthikkrishna-s/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective: https://www.presalescollective.com Timestamps 00:00 - Welcome and introduction 02:46 - Karthik's background and journey to presales 05:28 - What it means to "be in the room" for deal strategy 11:27 - Handling deals that aren't a good technical fit 16:30 - Building AE-SE relationships and trust 20:02 - Leveraging past customer experiences 27:14 - Growing strategic influence as an SE 32:30 - First experience in pipeline meetings and QBRs Key Topics Covered The Evolution of the SE Role From technical demonstrator to strategic partner Building relationships alongside technical expertise Flying "under the radar" while still influencing deals Co-Ownership vs. Support Understanding sales' responsibilities and pressures Taking appropriate accountability for deal outcomes Building a partnership model with Account Executives Strategic Influence Tactics Speaking up consistently, even when not initially heard Framing technical concerns alongside potential solutions Leveraging past experiences and customer success stories Cross-Functional Collaboration Involving product, implementation, and customer success teams Using collective wisdom to validate concerns Creating a "common voice" across departments Building Credibility Trust your instincts and speak up Demonstrate value through accurate deal insights Help teammates at critical junctures Bottom Line Solutions Engineers possess unique insights that can make or break deals, but gaining the opportunity to share those insights strategically requires building credibility, relationships, and influence over time. The most successful SEs find ways to contribute to deal strategy while respecting the unique pressures faced by their sales counterparts. Presales LIVE airs every other Tuesday. Join the Presales Collective Slack community to stay updated on future episodes, and follow the PSC LinkedIn page for upcoming shows.  

Today’s episode was recorded during Presales Collective’s AI-Powered Presales Summit on March 26th, 2025. In this episode, Jack Cochran (General Manager, Presales Collective) and co-host Matthew James discuss the ethics and trust issues surrounding AI in sales environments with guest Diana Capello, Director of Solutions Consulting for US and Demo Engineering at Eightfold. The discussion explores how AI is transforming the presales landscape, from creating demo environments to navigating AI buying committees and addressing hiring practices in tech. Diana shares insights from her 20-year journey in AI, offering valuable perspectives on maintaining customer trust while leveraging AI tools. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT / 11AM ET / 4PM GMT. Connect with Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Diana Capello: https://www.linkedin.com/in/dianacappello/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Book Recommendation, "AI Superpowers" by Kai-Fu Lee: https://www.goodreads.com/book/show/38242135-ai-superpowers  Presales Collective's YouTube channel: https://www.youtube.com/c/PreSalesCollective Presales AI Summit recordings, available on the PSC YouTube channel: https://www.youtube.com/@presalescollective7795  Timestamps 00:00 - Introduction 01:27 - Welcome Diana Cappello 04:10 - Maintaining customer trust while using AI 06:50 - Explaining how AI works to customers 11:45 - Navigating AI councils in enterprise sales 20:34 - AI in hiring processes 27:43 - Book recommendation 31:10 - Q&A  

In this episode, Jack Cochran (General Manager, Presales Collective) and guest co-host Allison Macalik dive into the topic of "Presales People in Disguise" with Alex Nation. They explore the journey into presales roles, the importance of effective discovery techniques, the power of silence in customer interactions, and the unique relationship between presales professionals and sales teams. Alex shares valuable insights from her career transition from retail to tech, highlighting key skills that have made her successful in the presales world. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Find us: Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/ Connect with Alex Nation: https://www.linkedin.com/in/alexandranation/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Timestamps 00:00 - Introduction 02:48 - Alex's background and journey into presales 08:59 - The importance of being a presenter pain point gatherer 10:40 - The power of effective discovery 14:24 - The art of silence in customer interactions 20:26 - Presales vs. Sales 26:20 - Advice to younger self 29:25 - How to find Alex Key Topics Covered Career Transitions into Presales Alex's journey from Nordstrom to tech Finding your strength as a "presenter pain point gatherer" The accidental path many take into presales roles Effective Discovery Techniques The importance of listening more than speaking How good discovery differentiates vendors Building trust with customers through purposeful questions The Power of Silence Using silence as a negotiation technique Training yourself to be comfortable with pauses Demonstrating confidence through patience Presales and Sales Dynamics Developing empathy for sales counterparts Understanding the complete customer lifecycle Working together for customer success Career Development The unique pressures and rewards of presales Developing flexibility and resilience Creating paths for women in presales