Ryan Flannelly’s Post

Is there an itch you’ve been looking to scratch in your enterprise sales role? Growing impatient with the glacial pace you often experience at big co - all the politics and red tape that get in the way of doing impactful work? Tired of being part of the machine versus building it? Seeing the writing on the wall that the product you’re selling isn’t at the innovative edge of cloud infrastructure or positioned to win the Global 2000 market? If this sounds familiar, it’s time to reboot your career at Pulumi. Pulumi helps 2,800+ customers and nearly 200,000 community members intelligently manage cloud infrastructure with a portfolio of expanding products: 🔥 Pulumi IaC - Industry leading open source infrastructure as code 🔥 Pulumi ESC - Secrets and configuration management reimagined 🔥 Pulumi Copilot - AI powered cloud infrastructure management The *right* seller recognizes that all of this = faster time-to-production for devs and reduces investment on development and production tools. A big win for leaders and developers alike. It also means a highly sellable product with growing marketing share. 👏 But hiring means nothing without investment in the function. That's why they've established ABX as a core GTM discipline to personalize every touchpoint in the B2B buyer journey and created first-class sales enablement and RevOps to succeed at scale - putting the team in a strong position to win larger accounts. With successful customers in almost every vertical and geography, adding GTM capacity allows this team to seize an opportunity ripe for the picking! Who are you? 👉 A proven enterprise seller looking to shape the intersection of AI and IaC to deliver continuously increasing value to the enterprise. 👉 A bit of a geek who loves talking tech problems with devs and SREs … but also has the gravitas to engage, listen and connect with CIO, CTO, and CISO execs.   👉 A builder who enjoys the imperfections that come with this stage of company maturity - seeing it as an opportunity to make impact beyond selling. 👉 You love to use a data-driven and analytical approach for opportunity pursuit, account planning and deal shaping. 👉 Your experience in both large enterprises and startups gives you a unique advantage, combining the strategic depth of big companies with the agility of startups to anticipate challenges and scale with precision. Who are they? 🧠 Some of the most brilliant minds in industry: Joe Duffy, Eric Rudder, Luke Hoban, Craig Symonds, Elenitsa Staykova, and Bob Laskey with backgrounds at Microsoft, GoPro, Cloudflare, and more  🚀 High-growth, Series C, global, fully remote 🏎 Setting cloud infrastructure industry trends, not just trying to keep up with them Madrona deeply believes in this team - that's why we backed them. Intrigued? You should be. Don’t just dream about the forefront of modern cloud infrastructure, be there writing the story. #enterprisesales #builders #cloudsales #hiringalert  

Think enterprise sales is just another roll of the dice? Consider it a chessboard where strategy reigns supreme. My career gave me the opportunity to be part of and build successful enterprise sales teams. I continue to help startups do this today through the sales and CS leaders they hire through my executive search firm. A word to the wise... If you’re starting from scratch, it takes at least 12–18 months to build a strong enterprise sales foundation. Founders, before you embark on this journey, take a hard look at your runway and run rate and ask the following questions: 📍 Do I know my niche?.. The riches are in the niches 💰 📍 Have I validated your ICP (one large customer is not validation)? 📍 Am I prepared to go to market? 📍 Do I have the infrastructure to customize and integrate? 📍 Am I ready, willing and able to delight my customers to hang on to them? 📍 Am I going after this segment based on perception or reality? Scale up only when you know the market responds well to what you're offering. And you can clearly articulate the 7 reasons why your customers engage and how you can help them: 1. Solve a problem 2. Reach a goal 3. Get better 4. Pinpoint blindspots they haven't yet considered 5. Be the hero of their story, not yours 6. Reduce/remove risk 7. Create a new or easier way to make money Over the weekend I heard the same nightmare story I hear all too often... A startup hiring a talented person in enterprise, wooing them out of their great job, to build up the same function for them... And then firing the person 3 months later when there isn't a pipeline. Folks, this isn't how true enterprise sales works. These are the 9 steps that never failed me as I was building this segment from scratch: 1. Ditch the shiny TAM objects and calculate the opportunity within your niche 2. Know your Ideal Customer Profile like the back of your hand (ICP) 3. Prioritize accounts that are the best fit 4. Research your prospects like you're in the FBI 5. Map out the business and multi-thread up, down, and across the company 6. Focus on discovery... always 7. Be relentless to deliver on your promise 8. Land and expand (the most low friction, efficient way to grow revenue) 9. Communicate early and often... even when you step in a pile of 💩 Validate first, nail, grow, and theeeeeeennnnnn scale. This is the formula for success. And it's not for the faint of heart. Trying to grow too quickly will only lead to mistakes in this market…and those are much harder to come back from with this type of customer. Pro tip: If you're running out of money and looking for a quick fix. This isn't the time to go after this segment. Remember, enterprise sales is a strategy to change the shape of a business... Not an experiment hoping to change the shape of yours. #startups #founders #sales #BuildWithATP

Job Title: Business Development Manager (BDM) - SaaS Sales Location: UK ,Remote Company Overview: Join the revolution at Haix AI, a pioneering force in cutting-edge technology within the social listening space. We are the first to offer a comprehensive suite covering all social platforms, news, Reddit, and more. Our first of a kind multi-model, multi-language AI-driven tool is entirely proprietary, putting us leaps and bounds ahead of the competition. At Haix AI, we disrupt the norm, and our team thrives on pushing boundaries. Position Overview: We are on the lookout for dynamic Business Development Managers (BDM) with a strong track record in selling SaaS solutions, particularly into the SMB and Enterprise sectors. While experience in social listening is preferred, it's not mandatory as we provide extensive product training. The successful candidate will showcase a deep understanding and competence in the 360-degree sales cycle, along with the ability to demonstrate ROI in a complex sales environment. Key Responsibilities: Execute the end-to-end sales cycle, demonstrating proficiency in all aspects. Target and secure new clients in both the SMB and Enterprise segments. Showcase the value proposition of our cutting-edge SaaS solutions. Illustrate ROI in complex sales scenarios. Cultivate and sustain strong client relationships for long-term partnerships. Embrace a hunter mentality with a can-do attitude. Qualifications: Minimum 5 years of sales experience, preferably in SaaS. Proven track record in successfully selling to SMB and Enterprise clients. Familiarity with social listening is advantageous but not mandatory. Strong understanding of the 360-degree sales cycle and the ability to showcase ROI. Self-motivated with a hunter mentality and a can-do attitude. Ability to thrive in an environment without micro-management. Interview Process: Telephone Interview: Initial discussion to assess qualifications and cultural fit. Video Interview: Deeper dive into experience and skills. On-the-Job Evaluation: Showcase your capabilities in a real-world scenario while demonstrating your ability to make an impact and generate revenue. This includes a commission-based component. Should you be successful on raising 6k GBP MRR new business in this period, you will be offered a 30k basic with a healthy commission and a you will have completed this stage and be offered a job with us. 9k GBP MRR in new business you will get offered a 40k basic plus commission, and for those that are bringing their A game and hit 15k MRR new business, we will offer you a 50k GBP basic. Think you’ve got what it takes then get in touch today!! Requirements: Proficiency in HubSpot, Microsoft 365, and Slack. Willingness to embrace and adapt to new technologies. Ability to thrive in a fast-paced, disruptive environment. If you're ready to be a part of a groundbreaking team, apply now to [email protected] with your CV. #saassales #businessdevelopment #BDMOpportunity #remoteworking #HaixAI

𝐔𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝𝐢𝐧𝐠 𝐭𝐡𝐞 𝐒𝐚𝐥𝐞𝐬 𝐂𝐲𝐜𝐥𝐞 𝐢𝐧 𝐒𝐚𝐚𝐒: 𝐈𝐦𝐩𝐥𝐢𝐜𝐚𝐭𝐢𝐨𝐧𝐬 𝐟𝐨𝐫 𝐇𝐢𝐫𝐢𝐧𝐠 The SaaS sales cycle is unique, often involving longer decision-making processes, complex customer needs, and ongoing relationships. Here’s how understanding the SaaS sales cycle can shape your hiring strategy: 1. 𝐋𝐨𝐧𝐠𝐞𝐫 𝐒𝐚𝐥𝐞𝐬 𝐂𝐲𝐜𝐥𝐞𝐬 𝐑𝐞𝐪𝐮𝐢𝐫𝐞 𝐏𝐚𝐭𝐢𝐞𝐧𝐜𝐞 𝐚𝐧𝐝 𝐏𝐞𝐫𝐬𝐢𝐬𝐭𝐞𝐧𝐜𝐞 🕰️ SaaS sales typically involve a longer buying process, with multiple touchpoints and decision-makers. When hiring, look for candidates who are patient, persistent, and capable of nurturing leads over time. They should be skilled at keeping prospects engaged without pushing for a quick close, ensuring deals progress steadily. 2. 𝐂𝐮𝐬𝐭𝐨𝐦𝐞𝐫-𝐂𝐞𝐧𝐭𝐫𝐢𝐜 𝐀𝐩𝐩𝐫𝐨𝐚𝐜𝐡 𝐢𝐬 𝐊𝐞𝐲 🎯 SaaS sales teams need to focus on solving customer problems, not just selling products. The ideal candidate should be customer-centric, with strong problem-solving skills and the ability to tailor solutions to meet specific client needs. Soft skills like empathy and active listening are essential for building trust and long-term relationships. 3. 𝐍𝐚𝐯𝐢𝐠𝐚𝐭𝐢𝐧𝐠 𝐂𝐨𝐦𝐩𝐥𝐞𝐱 𝐁𝐮𝐲𝐢𝐧𝐠 𝐏𝐫𝐨𝐜𝐞𝐬𝐬𝐞𝐬 𝐑𝐞𝐪𝐮𝐢𝐫𝐞𝐬 𝐄𝐱𝐩𝐞𝐫𝐭𝐢𝐬𝐞 🧠 SaaS deals often involve multiple stakeholders and complex negotiations. Look for sales professionals who have experience managing complex sales processes, working with diverse teams, and navigating decision-making hierarchies. Candidates should have excellent communication and negotiation skills to handle these multifaceted deals. 4. 𝐅𝐨𝐜𝐮𝐬 𝐨𝐧 𝐑𝐞𝐭𝐞𝐧𝐭𝐢𝐨𝐧 𝐚𝐧𝐝 𝐑𝐞𝐧𝐞𝐰𝐚𝐥𝐬 🌱 The SaaS model relies heavily on customer retention and renewals. Hiring salespeople with account management experience, who understand the importance of customer success and long-term engagement, is critical. They should be able to maintain relationships after the initial sale, ensuring clients see ongoing value in your solution. 5. 𝐀𝐝𝐚𝐩𝐭𝐚𝐛𝐢𝐥𝐢𝐭𝐲 𝐭𝐨 𝐚 𝐅𝐚𝐬𝐭-𝐂𝐡𝐚𝐧𝐠𝐢𝐧𝐠 𝐈𝐧𝐝𝐮𝐬𝐭𝐫𝐲 📈 The tech industry evolves quickly, and so do client needs. SaaS sales professionals must be adaptable and willing to continuously learn. When hiring, look for candidates who are agile, eager to stay up-to-date with industry trends, and can adjust their strategies to meet changing market demands. 𝐂𝐨𝐧𝐜𝐥𝐮𝐬𝐢𝐨𝐧 Understanding the SaaS sales cycle is crucial when building a sales team. The right hires will have the patience, problem-solving abilities, and adaptability needed to navigate long sales processes and foster lasting customer relationships, ultimately driving growth for your SaaS company. 💬 What qualities do you prioritize when hiring for SaaS sales roles? Share your thoughts in the comments! #SaaSSales #SalesHiring #SalesCycle #TechSales #CustomerRetention #BusinessGrowth

Nice topic for discussion. Several of the points you refer are quite true in terms of the emotional side of the sale and the associated risk and value perception from the contact. However, I would not agree to state that SMB are harder than Enterprise sales without providing more insights around the nature and challenges for both engagements. It is true that the decision making process is different and more straightforward in SMB space. However, the complexity of Enterprise sales is also tough as the amount of different stakeholders -which are usually part of the decision making process- with diverse roles, motivations and authority also makes that kind of sale quite hard, not to mention the complexity of the projects themselves. I think it might not be right to state whether one type of sales is harder than the other. It has also to deal with your own skillset and preferred sales approach. What do you think Lou Leuzzi

There are everyday opportunities and there are those opportunities that come once in a decade. There are transactional jobs and there are jobs that redefine a new and exceptional chapter. There are good leaders and there are great leaders whose way of leading make the difference 🤸♀️ If you want to be part of pioneering a new phase of growth here at Webpros, we want to talk to you. You could be a match if you are proactive, believe that when our customers and people win then the business win, you are culture & values driven, a strong executor who thrives in driving impact, incremental growth and raising the bar. You like to have fun, develop your skills and career while creating new possibilities... 👇 I am looking to engage with top talent for the roles below: 1. VP of Sales (AMER-Remote) - A strong people & customer centric leader, who knows how to drive growth in an existing customer base, experienced in the webhosting/software sales industry, commercially savvy and knows how to drive high performance with people and our partners success at the core of execution. 2. Sales Enablement Leader (EMEA-Remote/Fractional) - A leader who knows how to build skills and competencies for a customer centric sales operation, a tactical and strategic leader who can build from ground up and help facilitate growth and operational excellence 3. Senior Account Manager (AMER-Remote) - A growth focused individual with the ability to leverage our portfolio of solutions to drive growth for our biggest partners in an existing account base. You have experience in the web hosting industry, you are target driven, customer centric and have a growth mindset. You also get to work with a transparent, people focused and industry leader Thomas van Breen 4. Account manager (AMER- Remote) - A growth focused individual with ability to leverage our portfolio to drive growth for our small to medium partners in an existing account base, with experience in the web hosting industry. You are target driven, customer centric and have a growth mindset. You get to work with a growth minded and people focused leader Shoko Nagao 5. Global Partner Enablement leader (AMER-Remote) - One who is passionate to help drive growth, adoption, training and success for existing partners 6. Revenue Operations Manager (EMEA- Remote) - You are data driven, with a strong business acumen, a commercial and revenue growth mindset with insights to leverage data for operational efficiency. You get to work with an empathetic and execution leader Stefanie Langner Link to roles below, also feel free to inbox me or team to discuss further.. Have a productive week   #revenuegrowth #opportunity2024

SMB sales are harder than Enterprise sales. The SMB persona is tougher to navigate, the sales cycle is riskier, resources are slimmer, and cash is harder to part with. SMB buyers have more to lose: When selling to SMBs, you’re dealing directly with the business owner. This is someone who’s putting their own money on the line, and if your product fails, it could threaten their entire business. The decision-making process is deeply personal and emotional — their livelihood is at stake. In contrast, Enterprise sales involve a VP or department head. While they have something to lose — like their job or a promotion—their decision is less personal. The company won’t collapse if they make a mistake, and VPs tend to prioritize risk aversion over emotional considerations. You only have one shot on goal with SMB buyers: In SMB sales, if the owner says no, the deal is dead — potentially forever. You often have just one shot to make your case. On the other hand, Enterprise sales allow you to build a business case with multiple stakeholders. You get more shots on goal, which means more opportunities to navigate objections and push the deal forward. Enterprise sellers might argue that navigating procurement is challenging, but it’s really just another qualification process. Procurement’s job is to buy a product, not block it. Resources are limited with SMB sales processes: SMB AEs typically do it all: acting as BDR, AE, Sales Engineer, and Closer. Enterprise AEs manage much more complex sales cycles. Still, they have the resources to offset the added complexity — teams of BDRs, product-specific technical resources, and executive support to close the deal. SMB buyers are parting with their hard-earned cash; Enterprise buyers are not: In SMBs, business owners part with their cash. The emotional weight of spending personal money versus a company budget is massive. In Enterprise sales, VPs and department heads make decisions with someone else’s money, significantly reducing the emotional burden. Net... SMB sales is harder. …5, 4, 3, 2, 1 until the Enterprise sellers tell me why I’m wrong.

Nailed as always. Reposting for visibility to those building their Sales careers. 1. you should already be following Ryan - but in case you aren't - here's a highlight. 2. this is a pyramid 🔝 - there are only a few spots 'at the top'. you have to work hard - differentiate yourself, find great companies & possibly more importantly work with great mentor/coaches. 3. yes, sometimes it is just luck ☘ - being in the right place(company) right time(the idea/solution takes off). Sales is lucrative. It is not for the faint of heart. ❤️

Sales Series: Fast-Track Sales Success – A 90-Day Plan to Ramp Up Your Reps NetCom Learning is headquartered in NYC, and the majority of our sales come from the USA market. We will be aggressively adding a massive sales team in India and the UAE in the coming months to target the India and Middle East markets, while adding multiple Enterprise PODs in the USA to continue building on our strengths. Hiring and retaining great salespeople is brutally difficult and expensive. I also know the first 90 days can make or break a new rep’s success. A clear ramp-up plan is the key to turning new talent into high performers. Here’s what has worked for me: My 3-Phase Ramp-Up Plan to Get Your Sales Reps Performing in 90 Days: Phase 1: Onboarding & Training (Days 1-30) A strong start sets the tone for future performance. Without a solid foundation in product knowledge, the sales process, and clear goals, reps can easily get off track. 1. Goal Agreement, Product & Industry Knowledge: Begin with the end in mind. Set up clear input and output goals on day one. Ensure reps understand what they’re selling and who they’re selling to. Provide a deep dive into your product’s value proposition, industry trends, and competitors. 2. Sales Process Familiarization: Walk them through your sales funnel, from prospecting to closing. They need to see how each pipeline stage connects to the company’s goals. Process management is key to ramping up sales reps effectively. 3. Shadowing & Mock Calls: Pair new reps with top performers. Let them listen in on calls, learn how to handle objections, and practice real-life scenarios through mock calls. Phase 2: Activity & Prospecting (Days 31-60) This is where they start putting their training into action. The focus here is on building habits and generating activity. 1. Set Clear Activity Metrics: Establish daily/weekly goals—whether it’s calls made, emails sent, or meetings booked. These clear, attainable metrics show them what success looks like. 2. Prospecting Playbook: Provide targeted prospect lists, scripts, and templates. The goal is to get them into the rhythm of engaging prospects and building their own pipeline. 3. Feedback & Coaching Sessions: Meet regularly to review their progress and refine their approach. This helps them adapt quickly and focus on what works. Phase 3: Results & Closing (Days 61-90) By this stage, your reps should be building their pipeline and closing deals. 1. Pipeline Reviews & Strategy Sessions: Weekly reviews help identify where they should focus their efforts and how to move prospects through the funnel. 2. Focus on Early Wins: Encourage them to go after “quick win” opportunities. Early successes build confidence and drive momentum. 3. Accountability & Refinement: Keep tracking their activity and hold them accountable for hitting their numbers. Refining their approach is key to becoming more effective. Applied knowledge is powerful! #SalesLeadership #Onboarding #CEO #CRO

Tech sales career path 101: Break in as an entry tech level SDR **OTE $70k** Work really hard, set yourself apart Timeframe 9 months Parlay that into an SDR role at an established company **OTE $85k** Work really hard, set yourself apart Timeframe 1 year (salaries & top companies for SDRs: https://bit.ly/3wAbC5V) Parlay that into an SMB Acct Exec role (ideally same org) **OTE $120k** Work really hard, set yourself apart Timeframe 2 years (salaries & top companies for SMB account execs: https://bit.ly/4bQyRJ1) Parlay that into another AE role, larger deal size **OTE $175k** Ideally same org, but you could jump for the right opp Work really hard, set yourself apart Timeframe 3 years (salaries & top companies for mid market AEs: https://bit.ly/42WagOU) Now you have options. Take an account management role with higher base, lower upside, a bit ‘safer' of an option (salaries & top companies for account managers: https://bit.ly/3wsFwJ4) OR a customer success role if closing and prospecting isn't your thing (salaries & top companies for customer success: https://bit.ly/3TgxEnd) OR a sales engineering role if you're more into the technical side of things (salaries & top companies for sales engineers: https://bit.ly/3wsFukq) OR... Take a management role with higher base and OTE, but lower upside, but possibly puts you on track for the C-suite (would be another 5-7 years) (salaries & top companies for first line managers: https://bit.ly/3UXnCIL) OR... Stay on the AE track and: Parlay that into a strategic or enterprise AE role **OTE $300k** Work really hard, set yourself apart… and just make bank. Top performers in this role are clearing $1M/year. (salaries & top companies for strategic AEs: https://bit.ly/4bVBWaU) Every one of these transitions / decisions requires one constant: Work hard, set yourself apart. IT IS HARD. The winners do the hard things that sometimes suck. + Do what’s required. + Do things that you don’t really feel like doing today. + Do those things again tomorrow. + Do more of them next week and next month. + Make a few extra calls. + Send that follow up this evening instead of waiting until tomorrow. + Check in with deals you signed a few months back. + Don't complain because '1.5 years is too long to stick it out' The path to $1M is in front of you. But so is the path to 7 different companies over the next 10 years, never getting to your OTE. Some of it is out of your control. But frankly more of it is in control than you realize. ✌️