Salesloft MCP Demo Server

# Interview: Andrew Miller - Accounting/Tax Technology CRO ## Metadata | Field | Value | |-------|-------| | **Date** | January 14, 2025 | | **Duration** | 30 minutes | | **Interviewer** | Sarah Chen, Senior Sales Director, Salesloft + Clari | | **Interviewee** | Andrew Miller, Chief Revenue Officer, Accounting/Tax Technology (Titan Software) | | **Company ARR** | $175M | | **Focus Areas** | Sales enablement, revenue intelligence, seasonal buying cycles, market consolidation | --- ## Interview Transcript **[SALESLOFT REP]** Good morning, Andrew. Thanks so much for taking the time to chat with me today. I've been following Titan's growth in the accounting software space, and I'm really impressed with what you're building. Before we dive in, I'm curious—when you think about the sales challenges in the accounting and tax tech space right now, what's top of mind for you? **[ANDREW]** Sarah, I appreciate that. You know, it's a fascinating time to be in this space, but honestly, it's also incredibly complex. We're operating at this interesting intersection where we've got traditional tax and accounting firms that are still very much wedded to their desktop solutions—some are still on software from the early 2000s—and then you've got this newer generation of CPAs and bookkeepers who are cloud-native from day one. It's almost like we're selling into two different markets within the same market, if that makes sense. **[SALESLOFT REP]** That actually makes a lot of sense. And I imagine that seasonal complexity adds another layer, right? I know tax season is this huge buying window for accounting firms. **[ANDREW]** Yeah, so here's the thing—and this is probably counterintuitive for people outside the space—but the post-tax season window is actually where the real money is. During tax season, January through April, everyone's head-down in compliance work. They're not thinking about new software investments. They're barely thinking about anything except getting returns filed. But come May, June, July? That's when the conversations happen. That's when firms have the bandwidth to evaluate tools, run pilots, and make buying decisions. We typically see our biggest pipeline acceleration in Q2 and Q3, not in Q1. **[SALESLOFT REP]** So your sales and marketing strategy has to completely flip from what a lot of other SaaS companies do? **[ANDREW]** Completely. We're nurturing relationships heavily during tax season, but we're not pushing demos or heavy sales conversations. It's more about thought leadership, staying visible, and building trust. We might send a recorded webinar or a case study showing how a firm like theirs reduced compliance time. But a hard sell during tax season? That's tone-deaf. Partners are stressed, drowning in work. Then in May, when we see that their tax season workload drops off, that's when we can say, "Hey, remember us? Here's how we can make your life easier next year." And now they're actually receptive. **[SALESLOFT REP]** That's a really smart approach. So if you're forecasting revenue, you're probably building your go-to-market calendar backwards from that May-June window? **[ANDREW]** Exactly. Our entire marketing and sales calendar is built around that seasonal reality. We start relationship nurturing in October. By December, we're warming up more actively. Then tax season, we're providing value without selling. May hits, and we're ready to pounce with demos, ROI calculators, proof points. It's like the whole company operates on this 18-month sales cycle that's tied to the accounting calendar, not the calendar year. **[SALESLOFT REP]** I want to shift gears slightly. You mentioned this generational divide. Can you paint me a picture of what you're seeing in terms of buyer personas? **[ANDREW]** So on one end, you've got the traditional partner—usually 45 to 65 years old, been in their firm for 20-plus years, maybe owns a piece of it. They've seen plenty of technology failures. They're skeptical. They want proof, references, and they want to understand the implementation complexity. They're not on Twitter or LinkedIn consuming thought leadership. They're reading industry publications, maybe they're in an industry association. Their buying committee often includes the IT person, the office manager, maybe a senior manager or two. Then you've got the younger partners and managers—35 to 45—who came up after personal computers were already a thing. They're more open to cloud, they see the competitive advantage, but they still have to convince the senior partner who owns the firm. These folks are on LinkedIn, they've attended a few tech-focused conferences. They're actually pretty savvy about SaaS. And then the third persona is the Gen Z and millennial staff accountants. They've never used a legacy desktop solution in their professional life. They expect cloud-native tools, mobile access, the ability to work from anywhere. They're coming out of school with experience using modern software. When they hit a firm that's still on Sage 50 or CCH, they're shocked. And frankly, this is creating some attrition. Younger talent is choosing firms that have modern tech stacks. **[SALESLOFT REP]** So from a go-to-market perspective, you can't have one message or one channel that reaches all three of these personas? **[ANDREW]** Not even close. With the legacy partner, we're doing LinkedIn outreach that speaks to risk mitigation and business continuity. We're sponsoring industry events like state CPA societies. We're getting case studies into trade publications like CPA Practice Advisor. With the mid-market manager, we're doing paid social, we're running webinars, we're using sales development reps to build relationships. And with the staff level? We're probably reaching them through YouTube, TikTok, Discord communities around accounting—places where they're actually hanging out. **[SALESLOFT REP]** Wait, TikTok? For accounting software? **[ANDREW]** [Laughs] I know, I know. But yeah, there are these communities of young accountants and bookkeepers on TikTok and YouTube talking about the profession, venting about legacy tools, celebrating when they get to use cloud-based solutions. It's a real thing. If you want to influence the younger generation of talent, you have to meet them where they are. **[SALESLOFT REP]** That's really insightful. And I imagine that generational messaging also ties into the Big 4 influence you mentioned you're thinking about? **[ANDREW]** Oh, massively. Here's the reality: the Big 4 firms—Deloitte, EY, KPMG, PwC—they have massive advisory practices that push modern, integrated tech stacks. When they do an engagement with a mid-market accounting firm, they're often recommending enterprise-scale solutions. And mid-market firms listen to them. The Big 4 partner comes in and says, "You should look at this tool," and suddenly that tool is on the evaluation list. But here's the challenge for us: the Big 4 firms are pushing their own integrated platforms or they have preferred vendor relationships with massive players like Oracle, SAP, Microsoft. If you're not aligned with those ecosystems, it's hard to get traction in that channel. At the same time, the Big 4 influence is trickling down. Even the solo practitioners and small firms are being influenced by the fact that larger firms use certain tools. There's this halo effect. **[SALESLOFT REP]** Are you finding that the Big 4 recommendation is a barrier or an opportunity for Titan? **[ANDREW]** Both, honestly. It's a barrier when they're recommending an enterprise solution that's overbuilt for what an accounting firm needs. But it's an opportunity when we position ourselves as the specialized alternative. We say, "The Big 4 recommends these enterprise tools, but those are built for consultants managing complex global operations. You need accounting software built by accountants, for accountants." That positioning resonates with the mid-market that feels like enterprise solutions are bloated and expensive. **[SALESLOFT REP]** That positioning is interesting, and it ties into this best-of-breed versus embedded conversation, right? **[ANDREW]** Exactly. And this is probably the most existential challenge we're facing right now. Five years ago, the answer was clear: best-of-breed. You bought accounting software from us, tax software from one vendor, practice management from another, and you integrated them. That was the flexibility approach. But now you're seeing this massive push toward embedded accounting in ERP systems. Microsoft Dynamics, NetSuite, Workday—they all have accounting modules baked in. And they're positioning it as this integrated, all-in-one story. **[SALESLOFT REP]** Is that actually what firms want, or is it what vendors want? **[ANDREW]** [Pauses] That's a great question. I think it's both. The idea of having one platform that handles accounting, inventory, HR, supply chain—that's appealing from an operational perspective. But in practice, most accounting firms are specialized. They don't manage supply chains. They don't do inventory management. So they're paying for a ton of functionality they don't need, and the accounting module is often not as sophisticated as a best-of-breed solution. But here's where it gets tricky: the next generation of CFOs and financial leaders expect to work in an ERP environment. They're coming from larger companies where they used SAP or NetSuite. When they move to an accounting firm, they expect that integrated environment. So we're stuck. We can make the best specialized accounting software in the world, but if the buyer expects everything in one platform, we're fighting an uphill battle. **[SALESLOFT REP]** How are you thinking about positioning against that? **[ANDREW]** We're focusing on specialization as a strength, not a weakness. We're saying, "We've spent 20 years perfecting the accounting software experience. We're not trying to be everything to everyone. When you use our software, you're using the most advanced accounting platform available, and you can integrate it with whatever other tools you need." It's the old "best-of-breed" playbook, but we're acknowledging that integration is harder than an all-in-one platform. We're also building really strong integrations with the major ERPs. So if a firm is using NetSuite for their overall business but wants a better accounting experience, they can layer us on top. We're actually starting conversations with some enterprise clients where they're replacing the NetSuite accounting module with Titan. It's a niche play, but it's a profitable one. **[SALESLOFT REP]** That's smart. I want to talk about one more thing that I think is probably a huge sales objection—the cloud migration piece. We're talking about firms that are potentially still on desktop software from the 2000s, as you mentioned earlier. What are the barriers you're seeing to cloud migration? **[ANDREW]** Oh man, where do I start? [Laughs] First, there's the obvious one: it's hard to teach old dogs new tricks. Partners who've been using the same software for 20 years are used to how it works. There's this comfort level. They know where to click. Their team knows how to use it. The idea of retraining on something new feels like a big lift, even if that new tool is faster and more intuitive. But it goes deeper than that. There's actual risk, from their perspective. What if the cloud server goes down? What if their data is in the cloud and they can't access it? What about security and compliance? These are real concerns, not just FUD. Accounting firms handle sensitive client data. They have professional liability insurance. There's actual compliance requirements around data security. So when we ask them to move their data to the cloud, we're asking them to take what feels like a real risk. Then there's the economic question. The cost to migrate—both the software cost and the time cost of retraining staff—feels high. And the ROI is soft. It's not like you're buying a new delivery truck and suddenly you can deliver twice as many packages. You might save some time, you might reduce errors, but it's not quantified. So the decision is emotionally charged rather than analytically clear. **[SALESLOFT REP]** Is that where revenue intelligence and better sales execution comes in? Are you trying to quantify that ROI more tightly? **[ANDREW]** Absolutely. That's actually why I was interested in learning more about what Salesloft and Clari can do. Right now, when our sales reps are in conversations with firms, we have ROI calculators, we have case studies, but we don't have great insight into what's actually driving decision-making within those firms. We don't know if the conversation is stalling because the partner is genuinely skeptical or because they're just busy. We don't know if there's budget available. We don't know if there are internal champions building the case for us internally. If we could see into those conversations more clearly—if we knew that the VP of Operations at a firm was internally presenting our tool to partners, or if we could see that they'd downloaded multiple resources and were reading up on us—we could be much smarter about timing our outreach and crafting our messaging. **[SALESLOFT REP]** And that's especially critical given that seasonal buying window you described earlier, right? You need to know where a prospect is in their buying journey so you don't try to close them in March. **[ANDREW]** Yes. We waste so much effort and goodwill pushing in the wrong seasons. A great rep knows not to push during tax season. But we're still not great at knowing where a prospect is in the buying journey when post-tax season comes. Are they going to evaluate in May? July? Next year? Are they talking to three competitors or just us? Do they have budget? Understanding that would completely change how we prioritize and how we sequence our outreach. **[SALESLOFT REP]** Let me ask you this: if you could solve one problem with your sales process right now, what would it be? **[ANDREW]** [Thinks for a moment] Visibility into early-stage buying signals. Right now, our reps spend a lot of time pursuing deals that aren't real, or spending effort on deals that are real but they've already lost. We need better insight into which prospects are actually building internal consensus, which firms have budget, and where we stand relative to competitors. And we need that in a real-time way so we can respond quickly. The second thing is efficiency. We have great reps, but they're drowning in administrative work. They're manually tracking conversations, they're updating spreadsheets, they're trying to remember context from the last call. If we could automate that and give them back time to actually sell, we'd see a real productivity lift. I don't think we need to hire more reps—I think we need to make the ones we have more effective. **[SALESLOFT REP]** That makes sense. And I imagine as you're scaling, that leverage becomes even more important, right? You're growing the team, but you want productivity per rep to stay the same or improve? **[ANDREW]** Yeah. We've grown revenue almost 300% in the last three years, but we've been careful about team growth. We're hiring selectively. We want reps who fit our culture and our selling approach. But that means each rep has to own more of the revenue. We can't afford dead weight. And frankly, with the complexity of selling in this market—the seasonal patterns, the multiple buyer personas, the positioning challenges—our reps need all the help they can get. **[SALESLOFT REP]** Let me ask you about how you're thinking about competitive positioning. Obviously, you've got the big ERP players pushing embedded accounting. You've got legacy accounting software vendors who've been around forever. Where do you see Titan fitting in that landscape in five years? **[ANDREW]** I think the market is going to bifurcate. You're going to have the integrated, platform-based solution from the ERPs. They'll own a big portion of the market, especially for firms that need that broad functionality. But you're also going to have these specialized, best-of-breed solutions for firms that want the very best accounting experience. We're betting that the best-of-breed side of that bifurcation is growing, not shrinking. Younger firms, growth-minded firms, firms that are talent-driven—they want the best tools. They want the accounting software built by people who care most about accounting. The competitive moat we're building is deep specialization. We know accounting better than anyone else. We know the workflows, the pain points, the regulatory landscape. We're hiring accounting experts, former CPAs, people who spent years in the profession. And that expertise is going to show up in the product and in how we sell. **[SALESLOFT REP]** That's a compelling vision. And I think sales execution has to reflect that positioning, right? You can't sell a best-of-breed solution with a one-size-fits-all sales process. **[ANDREW]** Exactly. And that's where I think we're actually at a disadvantage compared to the big vendors. They have massive sales teams, they have huge marketing budgets, they have established relationships. We have to be smarter. We have to be more targeted. We have to understand our buyer better, we have to align our messaging better, and we have to respond faster to buying signals. It's basically a David and Goliath situation, except our David has some slingshots he hasn't fully loaded yet. **[SALESLOFT REP]** [Laughs] I like that. So in terms of what we could potentially help with—visibility, rep productivity, sales intelligence—where would you prioritize? What would have the biggest impact on your business? **[ANDREW]** If I'm honest, I'd say it's probably a two-part answer. First, I want better visibility into buying signals and account engagement. I want to understand, in the post-tax season window, which of our prospects are actually going to move. Second, I want to give my reps the tools to move faster and smarter. Right now, they're good, but they could be great if they had better information and less admin work. Beyond that, as we scale, I'm thinking about forecasting and predictability. We're a growing company, we're not yet mature. Our sales cycle is still variable. But to keep investors and partners confident, we need to get better at predicting revenue. If Clari can help us get to a 95% forecast accuracy, that's actually worth a lot more than just incremental sales lift. **[SALESLOFT REP]** That makes sense. And I think the forecasting piece is interesting because you've got these seasonal patterns, multiple buyer personas, longer sales cycles. That's exactly the kind of complexity where intelligence tools really shine. **[ANDREW]** Yeah. I mean, every company says they want better forecasting, but the challenge in our market is that the inputs are weird. We have this seasonal demand, we have multiple personas with different buying cycles, we're often selling to committees, not individuals. So what works for a typical SaaS company selling to a single buyer might not apply to us. **[SALESLOFT REP]** That's a great point, and honestly, that's the kind of nuance we need to understand during implementation. But I'm confident we can model for your specific market dynamics. Have you thought about a timeline for potentially exploring this? I know you're busy, especially with tax season ramping up. **[ANDREW]** [Laughs] Yeah, timing is terrible, right? But that's kind of the point. We know tax season is busy. But I'd be open to a conversation in May or June when things calm down. And maybe that conversation is with my VP of Sales and the sales leadership team. I'm involved strategically, but I want to make sure the team that's actually using the tools day-to-day has input on the decision. **[SALESLOFT REP]** That's really smart. And honestly, that's probably the right buying committee for a decision like this anyway. Can I follow up in May and schedule time with you and your VP of Sales? **[ANDREW]** Absolutely. And Sarah, I appreciate you asking about the context of our business before pitching solutions. A lot of vendors just launch into "Here's what we do," but you actually wanted to understand our market. That's refreshing. It tells me you're thinking about how to solve our problem, not just how to sell us something. **[SALESLOFT REP]** That's the only way it works, honestly. You're clearly thinking about a lot of complex challenges, and any solution we build together has to account for that. I'll send you a follow-up note, but let's calendar for early June? **[ANDREW]** Perfect. And in the meantime, if you want to talk to a few of our reps about what they see in the field, I'm happy to set that up. They'll give you the ground truth on what's working and what isn't. **[SALESLOFT REP]** I'd love that. Thanks so much, Andrew. This has been really enlightening. **[ANDREW]** Thanks, Sarah. Talk soon. --- ## Key Takeaways ### Market Dynamics - **Seasonal Buying Cycles**: The accounting software market operates inversely to tax season. Buying conversations cluster in Q2-Q3 (May-July), not during tax season (Jan-April). Sales and marketing strategies must be calibrated to this reality, emphasizing relationship nurturing during tax season rather than hard selling. ### Buyer Segmentation & Go-to-Market - **Three Distinct Personas**: Traditional partners (45-65, skeptical, offline channels), mid-market managers (35-45, more tech-savvy, digital channels), and younger staff (Gen Z/millennial, cloud-native, social platforms). No single message or channel reaches all three effectively. - **Generational Transition**: Younger accounting talent expects modern cloud-based tools and will leave firms stuck on legacy software. This is creating competitive pressure for mid-market firms to modernize. ### Enterprise & Big 4 Influence - **Big 4 Influence as Barrier & Opportunity**: The Big 4 firms push enterprise ERP solutions which creates a halo effect in the market. Positioned as a risk, but also an opportunity for best-of-breed solutions to differentiate as specialized alternatives. - **Channel Strategy Complexity**: Recommendations from Big 4 advisors heavily influence mid-market buying decisions. Direct vendor relationships with these firms are valuable but difficult to establish. ### Platform Consolidation vs. Specialization - **Embedded Accounting in ERP**: Enterprise platforms are embedding accounting modules, pushing toward all-in-one solutions. However, accounting firms don't need broader ERP functionality. Best-of-breed positioning ("specialization as strength") resonates with growth-minded firms. - **Differentiation Path**: Deep specialization, integration capabilities, and team expertise (hiring former CPAs) are key to competing against both legacy vendors and emerging platforms. ### Cloud Migration Barriers - **Technical & Psychological Resistance**: Firms are comfortable with legacy software they've used for 20+ years. Cloud migration feels risky (data security, compliance, downtime), expensive (retraining costs), and has soft ROI (time savings, error reduction are hard to quantify). - **Change Management**: The challenge isn't just technology adoption; it's organizational change management. Fear of risk, lack of clear ROI, and operational disruption make cloud migration decisions emotionally charged. ### Sales Execution Challenges - **Visibility Into Buying Signals**: Current tools don't provide insight into which firms are building internal consensus, have budget, or where Titan stands relative to competitors. Real-time buying signal visibility would transform go-to-market effectiveness. - **Rep Productivity & Efficiency**: Sales reps spend too much time on administrative work and lack context for conversations. Reducing admin burden and improving information flow could increase productivity without hiring. - **Forecasting Complexity**: Seasonal demand, multiple personas, longer sales cycles, and committee-based buying make traditional SaaS forecasting models insufficient. Need to model for market-specific dynamics. ### Strategic Priorities 1. **Immediate**: Visibility into early-stage buying signals and account engagement, especially timing of post-tax season pipeline 2. **Medium-term**: Reducing rep admin burden and improving conversation context 3. **Long-term**: Improving forecast accuracy and predictability for investor/partner confidence ### Timing & Next Steps - Ideal conversation timing: May-June (post-tax season) when sales leadership has bandwidth - Key stakeholders: VP of Sales and sales leadership team, along with CRO for strategic alignment - Opportunity to speak with field reps to understand ground truth on current challenges