In this episode, Jack Cochran and Matthew James are joined by Justin McDonald, Co-founder and CEO of Saleo, to discuss how demo automation technology is transforming the presales landscape. They explore the evolution of presales over the past 20 years, the hidden costs of demo preparation (the "demo tax"), and how AI is revolutionizing how solutions engineers create and personalize demonstrations. Justin shares insights on building relational capital, the importance of in-person meetings, and why the future of presales lies in leveraging technology to spend more quality time with buyers.

Thank you to Saleo for sponsoring this episode! Visit Saleo.io to learn more.

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Justin McDonald: https://www.linkedin.com/in/justin-mcdonald-21a3aa6/

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Saleo: https://saleo.io/

• Mockaroo (dummy data generator): https://mockaroo.com/

00:00 Welcome

04:24 How has presales evolved over 20 years

09:20 Demo tax

13:37 The importance of in-person meetings

15:55 Breaking down the demo tax components

24:47 AI and Demo Data Agents

26:42 Trends reshaping presales in 2026

1. The Evolution of Presales Technology

   • From manual data creation with tools like Mockaroo to automated demo environments

   • The rise of presales as a respected profession with executive leadership

   • Shift from multi-week prep and constant travel to efficient Zoom-based demos

2. The Demo Prep Tax

   • Multiple departments impacted: DevOps, product, engineering, and SEs

   • Hard dollar costs: hosting demo tenants can cost millions at scale

   • Demo data degradation: perfectly prepared demos degrade over time

   • SE time is expensive, and hours spent on manual data preparation adds up

3. Building Relational Capital

   • Only 17% of sales time is spent with buyers (even less for presales)

   • In-person interactions unlock opportunities that Zoom calls cannot

   • EQ and relationship-building will separate good from great in the age of AI

4. AI-Powered Demo Automation

   • Demo Data Agent: generates personalized demo data with a single prompt

   • Token-based customization for industry, vertical, and use case adaptation

   • Data injection technology allows real-time demo personalization

5. The Future of Presales

   • AI will expand automation across the entire sales cycle

   • Agentic and asynchronous AI tools will support SEs 24/7

   • SEs won't be replaced, their time will be used differently

   • The demo data is the story: great storytelling requires great demo data

In this episode, Jack Cochran and Matthew James are joined by Hannah Bloking, and Allison Macalik, co-founders of 4Under3. They discuss the universal challenge of imposter syndrome in the pre-sales profession, exploring how it manifests, why it affects nearly everyone, and practical strategies to address it. Hannah and Allison share insights from their workshops, including powerful techniques like the "lighthouse speaker" mindset and the importance of naming your imposter to take control of those negative thoughts.

Thank you to Storylane for sponsoring this episode.

Follow the Hosts and Guests

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Hannah Bloking: https://www.linkedin.com/in/hannahcfrisch/

• Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/

Links and Resources Mentioned

• Storylane: https://storylane.io

• Join Presales Collective: https://www.presalescollective.com/community-overview

• 4Under3: https://4under3.io/

• Email: info@4under3.io

• Follow 4Under3 on LinkedIn: https://www.linkedin.com/company/4under3/

Timestamps

00:00 Opening

03:36 Why Focus on Impostor Syndrome

11:57 The Definition of Impostor Syndrome

14:45 Redefinining as a Phenomenon

20:15 Soft Skills is Important

24:50 The Lighthouse Speaker Mindset

27:15 Zip it, Todd!

Key Topics Covered

1. Understanding Imposter Syndrome

   • The textbook definition: "The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills"

   • Why it's being reframed as "imposter phenomenon" rather than syndrome

   • How it manifests differently for everyone

   • The discovery that it affects people of all genders, levels, and backgrounds

2. The Presales Connection

   • Why imposter syndrome is particularly prevalent in pre-sales roles

   • The challenge of being asked to be an expert when you're still learning

   • Why internal demos to your own team are the hardest presentations to give

   • The adrenaline rush of presenting and how it relates to imposter feelings

3. Breaking the Silence

   • Why people suffer in silence with imposter syndrome

   • The power of creating space for vulnerability before major initiatives

   • How company culture needs to embrace these conversations

   • The importance of repeat workshops and ongoing dialogue

4. Practical Techniques

   • The Lighthouse Speaker vs. Spotlight Speaker: Thinking of yourself as lighting the way for others rather than being under scrutiny

   • Naming Your Imposter: Giving your negative self-talk a name (like "Todd") to externalize and control it

   • Reframing: Documenting what happens to realize most failures aren't actually about you

   • Finding Your Person: Identifying someone who can hold you accountable when your imposter is talking

5. The Workshop Impact

   • Why companies become repeat customers

   • How addressing imposter syndrome improves productivity and retention

   • The connection between soft skills training and embracing new frameworks

   • Creating internal communities (like AWS's "The Nest") for ongoing support

6. Looking Forward

   • The personal nature of addressing imposter syndrome

   • The importance of daily practice and repetition

   • How workshops facilitate conversations but individuals must do the work

   • The evolving nature of imposter syndrome as AI and change management accelerate

In this episode, Jack Cochran and Matthew James welcome Miriam Graf, a presales veteran with 20 years as an individual contributor and 10 years in leadership roles. Miriam shares invaluable insights on navigating career growth in presales, from speaking up about your aspirations to recognizing when leadership is and isn't the right path for you. She discusses the evolution from being "the hero" to becoming a leader who helps others shine, and explores the diverse career opportunities available beyond traditional management roles.

This episode is sponsored by Elvance. Find out more about them at https://elvance.io/

Follow Us

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Miriam Graf: https://www.linkedin.com/in/miriamgraf/ or email migraf3@gmail.com

Links and Resources Mentioned

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Presales Podcast: https://www.presalescollective.com/podcast

Timestamps

00:00 Welcome

06:53 Lessons to learn earlier

10:38 IC vs leadership

16:42 Expensive experience lessons

22:46 Variety of expertise is good

28:27 Focus on your industry and keep learning

Key Topics Covered

1. Speaking Up About Your Career

   • Why waiting for someone to notice doesn't work

   • How expressing interest puts you on the radar for future opportunities

   • The importance of taking initiative on projects you're passionate about

2. The Transition from Hero to Leader

   • Why being the top SE doesn't automatically translate to leadership

   • The emotional shift from personal accolades to team success

   • Understanding if management is actually the right path for you

3. Alternative Career Paths Beyond Management

   • National expert or technical specialist roles

   • Product management and product marketing opportunities

   • Customer success, implementation, and demo engineering

   • How presales skills translate across multiple disciplines

4. Essential Skills for Career Advancement

   • Soft skills: passion, communication, empathy, and listening

   • Business acumen: understanding the "so what?" for your audience

   • Technical skills: continuous learning and adaptability

5. Learning Through Experience

   • The value of trying roles outside presales

   • How diverse experience makes you a better SE

   • Why failures and tough feedback lead to growth

6. Industry Expertise

   • How to quickly learn an industry's key challenges

   • The value of becoming a vertical expert

   • Building credibility without years of industry experience

In this episode, Jack Cochran and Matthew James are joined by Rob Bruce, a presales leader at Syndigo with 20 years of experience, to discuss an innovative approach to presales operations: the Pursuit Desk. Rob shares how Syndigo has built a dedicated "concierge team" that handles RFPs, security questionnaires, reference coordination, and other time-consuming tasks, freeing solutions engineers to focus on discovery, solutioning, and building customer relationships. The conversation explores how to operate at the "top of your license," the role of AI in scaling pursuit operations, and practical advice for championing similar initiatives at your organization.

Thank you to Elvance for sponsoring this episode: https://elvance.io

Follow Us

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Rob Bruce: https://www.linkedin.com/in/robbruce/

Links and Resources Mentioned

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Book: "Selling is Hard, Buying is Harder" by Garen Hess

Timestamps

00:00 Welcome

04:29 What is a Presales Concierge

11:18 Presales culture

14:00 Working at the top of your diploma

17:10 How do you justify this

21:38 As focused as an F1 team

23:32 AI and the Pursuit Desk

Key Topics Covered

1. The Pursuit Desk Concept

   • Functions as a presales concierge handling non-customer-facing tasks

   • Manages RFPs, InfoSec documents, NDAs, reference coordination

   • Creates centralized control over messaging and responses

   • Operates on a global scale with cultural sensitivity

2. Operating at the Top of Your License

   • Focus on discovery, creative thinking, empathetic listening, and presenting solutions

   • Eliminate time spent on administrative tasks that don't require SE expertise

   • Reduce context switching and multitasking to maintain flow

   • Maximize value delivery to customers and the organization

3. Building the Business Case

   • Find an executive sponsor to champion the initiative

   • Measure impact through deal win rates and velocity

   • Consider creative budget reallocation (travel budgets, etc.)

   • Calculate ROI based on SE productivity and reduced burnout

4. The Role of AI in Pursuit Operations

   • AI handles first-pass RFP responses (80% completion)

   • Pursuit desk personalizes and adds empathy (final 20%)

   • Machine learning analyzes past deals for pattern recognition

   • Go/no-go scorecards based on historical data

   • Enables scaling without proportional headcount increases

5. Presales Culture and Values

   • Building trust through technical expertise and genuine personality

   • Being a "chameleon" who adapts to different buyer needs

   • Creating an environment where people feel welcomed and valued

   • Mentorship and knowledge sharing across teams

6. Preventing Burnout

   • Eliminating nights and weekends spent on RFPs

   • Reducing stress through better task distribution

   • Enabling SEs to focus on work they're passionate about

   • Creating sustainable workloads that retain top talent

7. Measuring Success

   • Tracking time spent on each RFP or pursuit activity

   • Correlating effort to win-loss rates

   • Building audit trails for continuous improvement

   • Creating dashboards for data-driven decision making

In this episode, Jack Cochran and Matthew James are joined by Art Fromm, author of "Making Seamless Sales" and sales enablement expert, to discuss how presales and sales teams can work together more effectively. Art shares insights from his 25+ years in sales enablement, exploring the common disconnects between SEs and AEs, and provides practical strategies for building stronger partnerships that drive better outcomes.

The conversation covers the evolution from tribal knowledge to systematic collaboration, the importance of discovery before demos, and how to create value perception rather than just showing features. Art emphasizes that when teams work together properly versus teams that don't, there's a 37% difference in sales outcomes - a substantial opportunity sitting on the table.

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 Art Fromm: https://www.linkedin.com/in/artfromm/

Links and Resources Mentioned

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Art's Website: https://teamsalesdevelopment.com

• Team Sales Development: https://www.teamsalesdevelopment.com

• "Making Seamless Sales" by Art Fromm: https://teamsalesdevelopment.com/making-seamless-sales-book/

Timestamps

00:00 Welcome

03:55 Sol/Con East 2025

05:26 Making SEAMless Sales

11:27 Our Solutions Have No Value

24:02 You Only Get One Shot

29:42 Aren't We All Presales

Key Topics Covered

1. The SEAM Framework

   • SE (Solutions Engineers) and AM (Account Managers) working together

   • Breaking down organizational silos between presales and sales

   • Creating systematic approaches rather than leaving collaboration to chance

2. Moving Beyond the Demo Rush

   • Why "we need to do a demo" often leads to failure

   • The importance of proper qualification and discovery first

   • How luck can reinforce bad habits in sales processes

3. Creating Value Perception

   • Understanding that solutions have no inherent value

   • The Venn diagram of customer needs overlapping with solutions

   • Turning "sell" into "buy" and "push" into "pull"

4. The Trust Dynamic

   • Presales comes with trust that can be lost

   • Sales lacks trust that needs to be gained

   • How proper discovery helps both teams build credibility

5. Organizational Alignment

   • Top-down (business focused) vs bottom-up (technical focused) approach

   • Creating healthy overlap between sales and presales responsibilities

   • The pyramid model of customer engagement levels

6. Training and Enablement

   • Moving beyond feature-function training to client success thinking

   • Understanding the complete buyer journey from hello to consumption

   • The concept of "solution enablement" as a continuous process

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

1. 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

2. 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

3. 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

4. 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: akash@tryopine.com

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

1. 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

2. 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

3. 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

4. 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

5. Practical AI Implementation

   • Draft-and-approve workflows for deliverables

   • Automating account research, meeting prep, and RFP responses

   • Using AI for onboarding and knowledge enablement

6. 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

1. 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

2. 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

3. The Rocks, Pebbles, Sand Framework

   • Planning for big quarterly tasks (rocks)

   • Managing predictable weekly activities (pebbles)

   • Handling unexpected fire drills (sand)

4. 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

5. 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